Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators

Jeong, Hyangsoo; Ng, Victor W.  L.; Börner, Janna; Schrock, Richard R.

doi:10.1021/acs.macromol.5b00264

Title: Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators

Abstract

Ring-opening metathesis polymerization (ROMP) of methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (PhEtNNBE; (S) and racemic) was researched employing six molybdenum and tungsten imido alkylidene initiators and two tungsten oxo alkylidene initiators. Of the six initiators that we introduced should yield cis,syndiotactic-poly[(S)-PhEtNNBE], two molybdenum OHMT alkylidene initiators, Mo(NR)(CHMe₂Ph)(pyr)(OHMT) (R = 1-adamantyl (Ad) or 2,6-Me₂C₆H₃ (Ar'); OHMT = O-2,6-mesityl₂C₆H₃; pyr = pyrrolide), and two tungsten oxo alkylidene initiators, W(O)(CHMe₂Ph)(2,5-dimethylpyrrolide)(PMe₂Ph)(OR) (OR = OHMT or (R)-OBr₂Bitet where (R)-Br₂BitetOH = (R)-3,3'-dibromo-2'-(tert-butyldimethylsilyloxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2-ol), produced essentially pure cis,syndiotactic-poly[(S)-PhEtNNBE]. Essentially pure cis,isotactic-poly[(S)-PhEtNNBE] was formed when (S)-PhEtNNBE was polymerized by Mo(NAr')(CHCMe₂Ph)(OBiphen_CF3)(thf) or W(NAr')(CHCMe₂Ph)((S)-OBiphen_Me) (OBiphen_CF3= 3,3'-di-tert-butyl-5,5'-bistrifluoromethyl-6,6'-dimethyl-1,1'-biphenyl-2,2'-diolate; (S)-OBiphen_Me = 3,3'-di-tert-butyl-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diolate). The best initiator for ROMP of rac-PhEtNNBE was Mo(NAd)(CHMe₂Ph)(pyr)(OHMT) at 0 °C, which led to a polymer that is biased (~80%) toward a cis,syndiotactic structure and that contains alternating enantiomers in the chain (cis,syndio,alt-poly[(rac)-PhEtNNBE]).

Authors:

Jeong, Hyangsoo ^[1]; Ng, Victor W. L. ^[1]; Börner, Janna ^[1]; Schrock, Richard R. ^[1]

Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)

Publication Date:: Tue Mar 17 00:00:00 EDT 2015

Research Org.:: Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)

Sponsoring Org.:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

OSTI Identifier:: 1557799

Grant/Contract Number:: FG02-86ER13564

Resource Type:: Accepted Manuscript

Journal Name:: Macromolecules

Additional Journal Information:: Journal Volume: 48; Journal Issue: 7; Journal ID: ISSN 0024-9297

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Jeong, Hyangsoo, Ng, Victor W.  L., Börner, Janna, and Schrock, Richard R. Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators.  United States: N. p., 2015. 
Web.  doi:10.1021/acs.macromol.5b00264.

Copy to clipboard


                    Jeong, Hyangsoo, Ng, Victor W.  L., Börner, Janna, & Schrock, Richard R. Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators.  United States.  https://doi.org/10.1021/acs.macromol.5b00264

Copy to clipboard


                    Jeong, Hyangsoo, Ng, Victor W.  L., Börner, Janna, and Schrock, Richard R. Tue .  
"Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators".  United States.  https://doi.org/10.1021/acs.macromol.5b00264.  https://www.osti.gov/servlets/purl/1557799.

Copy to clipboard


                    
@article{osti_1557799,

  title        = {Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators},

  author       = {Jeong, Hyangsoo and Ng, Victor W.  L. and Börner, Janna and Schrock, Richard R.},

  abstractNote = {Ring-opening metathesis polymerization (ROMP) of methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate (PhEtNNBE; (S) and racemic) was researched employing six molybdenum and tungsten imido alkylidene initiators and two tungsten oxo alkylidene initiators. Of the six initiators that we introduced should yield cis,syndiotactic-poly[(S)-PhEtNNBE], two molybdenum OHMT alkylidene initiators, Mo(NR)(CHMe2Ph)(pyr)(OHMT) (R = 1-adamantyl (Ad) or 2,6-Me2C6H3 (Ar'); OHMT = O-2,6-mesityl2C6H3; pyr = pyrrolide), and two tungsten oxo alkylidene initiators, W(O)(CHMe2Ph)(2,5-dimethylpyrrolide)(PMe2Ph)(OR) (OR = OHMT or (R)-OBr2Bitet where (R)-Br2BitetOH = (R)-3,3'-dibromo-2'-(tert-butyldimethylsilyloxy)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2-ol), produced essentially pure cis,syndiotactic-poly[(S)-PhEtNNBE]. Essentially pure cis,isotactic-poly[(S)-PhEtNNBE] was formed when (S)-PhEtNNBE was polymerized by Mo(NAr')(CHCMe2Ph)(OBiphenCF3)(thf) or W(NAr')(CHCMe2Ph)((S)-OBiphenMe) (OBiphenCF3 = 3,3'-di-tert-butyl-5,5'-bistrifluoromethyl-6,6'-dimethyl-1,1'-biphenyl-2,2'-diolate; (S)-OBiphenMe = 3,3'-di-tert-butyl-5,5',6,6'-tetramethyl-1,1'-biphenyl-2,2'-diolate). The best initiator for ROMP of rac-PhEtNNBE was Mo(NAd)(CHMe2Ph)(pyr)(OHMT) at 0 °C, which led to a polymer that is biased (~80%) toward a cis,syndiotactic structure and that contains alternating enantiomers in the chain (cis,syndio,alt-poly[(rac)-PhEtNNBE]).},

  doi          = {10.1021/acs.macromol.5b00264},

  journal      = {Macromolecules},

  number       = 7,

  volume       = 48,

  place        = {United States},

  year         = {Tue Mar 17 00:00:00 EDT 2015},

  month        = {Tue Mar 17 00:00:00 EDT 2015}

}

Copy to clipboard

Journal Article:

Free Publicly Available Full Text

Accepted Manuscript (DOE)

Publisher's Version of Record

https://doi.org/10.1021/acs.macromol.5b00264

Other availability

Search WorldCat to find libraries that may hold this journal

Citation Metrics:

Cited by: 19 works

Citation information provided by
Web of Science

Save / Share:

Export Metadata

Save to My Library

Works referenced in this record:

High Oxidation State Multiple Metal−Carbon Bonds
journal, January 2002

Schrock, Richard R.
Chemical Reviews, Vol. 102, Issue 1
DOI: 10.1021/cr0103726

Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts
journal, October 2003

Schrock, Richard R.; Hoveyda, Amir H.
Angewandte Chemie International Edition, Vol. 42, Issue 38, p. 4592-4633
DOI: 10.1002/anie.200300576

Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry
journal, August 2009

Schrock, Richard R.
Chemical Reviews, Vol. 109, Issue 8
DOI: 10.1021/cr800502p

Transition metal–carbon multiple bonds
journal, January 2001

Schrock, Richard R.
Journal of the Chemical Society, Dalton Transactions, Issue 18
DOI: 10.1039/b104609h

Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts ^†
journal, March 2010

Vougioukalakis, Georgios C.; Grubbs, Robert H.
Chemical Reviews, Vol. 110, Issue 3
DOI: 10.1021/cr9002424

Synthesis of stereoregular ROMP polymers using molybdenum and tungsten imido alkylidene initiators
journal, May 2011

Schrock, Richard R.
Dalton Transactions, Vol. 40, Issue 29, p. 7484-7495
DOI: 10.1039/c1dt10215j

Synthesis of Stereoregular Polymers through Ring-Opening Metathesis Polymerization
journal, June 2014

Schrock, Richard R.
Accounts of Chemical Research, Vol. 47, Issue 8
DOI: 10.1021/ar500139s

Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide Complex
journal, June 2009

Flook, Margaret M.; Jiang, Annie J.; Schrock, Richard R.
Journal of the American Chemical Society, Vol. 131, Issue 23, p. 7962-7963
DOI: 10.1021/ja902738u

Z-Selective and Syndioselective Ring-Opening Metathesis Polymerization (ROMP) Initiated by Monoaryloxidepyrrolide (MAP) Catalysts
journal, September 2010

Flook, Margaret M.; Gerber, Laura C. H.; Debelouchina, Galia T.
Macromolecules, Vol. 43, Issue 18, p. 7515-7522
DOI: 10.1021/ma101375v

Synthesis of cis,syndiotactic ROMP Polymers Containing Alternating Enantiomers
journal, January 2011

Flook, Margaret M.; Ng, Victor W. L.; Schrock, Richard R.
Journal of the American Chemical Society, Vol. 133, Issue 6, p. 1784-1786
DOI: 10.1021/ja110949f

Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate
journal, January 1990

Stella, L.; Abraham, H.; Feneau-Dupont, J.
Tetrahedron Letters, Vol. 31, Issue 18
DOI: 10.1016/0040-4039(90)80136-A

Ring opening metathesis polymerization of methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
journal, January 1997

Schitter, Regina M. E.; Steinhäusler, Thomas; Stelzer, Franz
Journal of Molecular Catalysis A: Chemical, Vol. 115, Issue 1
DOI: 10.1016/S1381-1169(96)00081-7

Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes
journal, December 2011

Peryshkov, Dmitry V.; Schrock, Richard R.; Takase, Michael K.
Journal of the American Chemical Society, Vol. 133, Issue 51, p. 20754-20757
DOI: 10.1021/ja210349m

Understanding d ⁰ -Olefin Metathesis Catalysts: Which Metal, Which Ligands?
journal, July 2007

Poater, Albert; Solans-Monfort, Xavier; Clot, Eric
Journal of the American Chemical Society, Vol. 129, Issue 26
DOI: 10.1021/ja070625y

Inversion of Configuration at the Metal in Diastereomeric Imido Alkylidene Monoaryloxide Monopyrrolide Complexes of Molybdenum
journal, January 2009

Marinescu, Smaranda C.; Schrock, Richard R.; Li, Bo
Journal of the American Chemical Society, Vol. 131, Issue 1
DOI: 10.1021/ja808308e

Fundamental Studies of Tungsten Alkylidene Imido Monoalkoxidepyrrolide Complexes
journal, June 2009

Jiang, Annie J.; Simpson, Jeffrey H.; Müller, Peter
Journal of the American Chemical Society, Vol. 131, Issue 22
DOI: 10.1021/ja9012694

Fundamental Studies of Molybdenum and Tungsten Methylidene and Metallacyclobutane Complexes ^†
journal, November 2010

Schrock, Richard R.; Jiang, Annie J.; Marinescu, Smaranda C.
Organometallics, Vol. 29, Issue 21
DOI: 10.1021/om100363g

Stereomutation in Trigonal-Bipyramidal Systems: A Unified Picture
journal, August 2011

Moberg, Christina
Angewandte Chemie International Edition, Vol. 50, Issue 44
DOI: 10.1002/anie.201103375

Stereospecific Ring-Opening Metathesis Polymerization of Norbornadienes Employing Tungsten Oxo Alkylidene Initiators
journal, July 2014

Forrest, William P.; Weis, Jonathan G.; John, Jeremy M.
Journal of the American Chemical Society, Vol. 136, Issue 31
DOI: 10.1021/ja506446n

Synthesis of a poly(2-azanorbornene) with a high degree of cis-TT-stereoregularity and a regular secondary solution structure
journal, January 2012

Rossegger, Elisabeth; Oláh, László; Fischer, Roland
Polymer Chemistry, Vol. 3, Issue 10
DOI: 10.1039/c2py20219k

Bipyridine Adducts of Molybdenum Imido Alkylidene and Imido Alkylidyne Complexes
journal, May 2012

Lichtscheidl, Alejandro G.; Ng, Victor W. L.; Müller, Peter
Organometallics, Vol. 31, Issue 12
DOI: 10.1021/om300353e

Syntheses of Tungsten tert-Butylimido and Adamantylimido Alkylidene Complexes Employing Pyridinium Chloride As the Acid
journal, August 2012

Jeong, Hyangsoo; Axtell, Jonathan C.; Török, Bela
Organometallics, Vol. 31, Issue 18, p. 6522-6525
DOI: 10.1021/om300799q

Molybdenum Imido Alkylidene Metathesis Catalysts That Contain Electron-Withdrawing Biphenolates or Binaphtholates
journal, April 2007

Singh, Rojendra; Czekelius, Constantin; Schrock, Richard R.
Organometallics, Vol. 26, Issue 10
DOI: 10.1021/om061134+

Alkylidene and Metalacyclic Complexes of Tungsten that Contain a Chiral Biphenoxide Ligand. Synthesis, Asymmetric Ring-Closing Metathesis, and Mechanistic Investigations
journal, March 2003

Tsang, W. C. Peter; Hultzsch, Kai C.; Alexander, John B.
Journal of the American Chemical Society, Vol. 125, Issue 9
DOI: 10.1021/ja0210603

Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands
journal, September 2014

Townsend, Erik M.; Hyvl, Jakub; Forrest, William P.
Organometallics, Vol. 33, Issue 19
DOI: 10.1021/om500655n

Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis
journal, November 2008

Malcolmson, Steven J.; Meek, Simon J.; Sattely, Elizabeth S.
Nature, Vol. 456, Issue 7224
DOI: 10.1038/nature07594

Works referencing / citing this record:

Functional Precision Polymers via Stereo- and Regioselective Polymerization Using Group 6 Metal Alkylidene and Group 6 and 8 Metal Alkylidene N -Heterocyclic Carbene Complexes
journal, August 2018

Buchmeiser, Michael R.
Macromolecular Rapid Communications, Vol. 40, Issue 1
DOI: 10.1002/marc.201800492

Similar Records in DOE PAGES and OSTI.GOV collections:

Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of endo -Dicyclopentadiene by Molybdenum and Tungsten Catalysts

Journal Article Autenrieth, Benjamin ; Jeong, Hyangsoo ; Forrest, William P. ; ... - Macromolecules

Here we report an examination of the ring-opening metathesis polymerization (ROMP) of endo-dicyclopentadiene (DCPD) by 10 well-defined molybdenum-based and 16 tungsten-based alkylidene initiators. Five tungsten-based MAP (monoaryloxide pyrrolide) initiators with the general formula W(X)(CHCMe₂Ph)(Me₂Pyr)(OAr) (X = arylimido, alkylimido, or oxo; Me₂Pyr =2,5-dimethylpyrrolide; OAr = an aryloxide) were found to yield >98% cis, >98% syndiotactic poly(DCPD); they are W(N-t-Bu)(CHCMe₃)(pyr)(OHMT) (2, OHMT = O-2,6-(2,4,6-Me₃C₆H₂)₂C₆H₃, pyr = pyrrolide), W(N-2,6-i-Pr₂C₆H₃)(CHCMe₂Ph)(pyr)(OHMT) (3), W(O)(CHCMe₂Ph)(Me₂Pyr)(OHMT)(PPh₂Me) (7, Me₂Pyr =2,5-dimethylpyrrolide), W(O)(CHCMe₂Ph)(Me₂Pyr)(ODFT)(PPh₂Me) (9, ODFT = O-2,6-(C₆F₅)₂C₆H₃), and W(O)(CHCMe₂Ph)(Me₂Pyr)(OTPP)(PMePh₂) (10, OTPP = O-2,3,5,6-Ph₄C₆H). Two biphenolate alkylidene complexes, Mo(N-2,6-Me₂C₆H₃)(CHCMe₂Ph)(rac-biphen) (17) and W(N-2,6-Me₂C₆H₃)(CHCMe₂Ph)(rac-biphen) (22, biphen =3,3'-(t-Bu)₂-5,5'-6,6'-(CH₃)₄-1,1'-biphenyl-2,2'-diolate), were found to yield >98% cis, >98%more »« less
Cited by 64
https://doi.org/10.1021/acs.macromol.5b00123

Full Text Available
Stereospecific Ring-Opening Metathesis Polymerization (ROMP) of Norbornene and Tetracyclododecene by Mo and W Initiators

Journal Article Autenrieth, Benjamin ; Schrock, Richard R. - Macromolecules

Here we report the synthesis of >98% cis,isotactic and cis,syndiotactic polynorbornene (poly(NBE)) and poly(endo,anti-tetracyclododecene) (poly(TCD)). Cis,isotactic poly(NBE) and poly(TCD) were prepared employing Mo-based biphenolate imido alkylidene initiators, Mo(NR)(CHCMe₂Ph)(Biphen) (Biphen = e.g., 3,3'-(t-Bu)2-5,5'-6,6'-(CH₃)4-1,1'-biphenyl-2,2'-diolate), while cis,syndiotactic poly(NBE) and poly(TCD) were prepared employing W-based imido or oxo monoaryloxide pyrrolide (MAP) initiators, W(X)(CHR')(Pyrrolide)(OTer) (X = NR or O; OTer = a 2,6-terphenoxide). Addition of 1-hexene or coordinating solvents such as THF do not decrease the stereospecificity of the polymerization. Cis,iso and cis,syndio dyads can be distinguished through investigation of ¹H and ¹³C NMR spectra of the two polymers in a mixture. The polymers weremore »« less
Cited by 55
https://doi.org/10.1021/acs.macromol.5b00161

Full Text Available
Formation of Alternating trans - A - alt - B Copolymers through Ring-Opening Metathesis Polymerization Initiated by Molybdenum Imido Alkylidene Complexes

Journal Article Jeong, Hyangsoo ; John, Jeremy M. ; Schrock, Richard R. - Organometallics

Ring-opening metathesis polymerization (ROMP) is enabled to prepare trans-poly(A-alt-B) polymers from a 1:1 mixture of A and B where A is a cyclic olefin such as cyclooctene (A₁) or cycloheptene (A₂) and B is a large norbornadiene or norbornene derivative such as 2,3-dicarbomethoxy-7-isopropylidenenorbornadiene (B₁) or dimethylspirobicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate-7,1'-cyclopropane (B₂). The most successful initiators that were examined are of the type Mo(NR)(CHCMe₂Ph)[OCMe(CF₃)₂]₂ (R = 2,6-Me₂C₆H₃ (1) or 2,6-i-Pr₂C₆H₃ (2)). The trans configuration of the AB linkages is proposed to result from the steric demand of B. Both anti-MB and syn-MB alkylidenes are observed during the copolymerization, where B was last inserted into amore »« less
Cited by 21
https://doi.org/10.1021/acs.organomet.5b00709

Full Text Available
Living cyclopolymerization of 1,6-heptadiyne derivatives using well-defined alkylidene complexes. Polymerization mechanism, polymer structure, and polymer properties

Journal Article Fox, H H ; Wolf, M O ; O'Dell, R ; ... - Journal of the American Chemical Society; (United States)

We report here the living cyclopolymerization of 1,6-heptadiyne derivatives (usually 4,4-disubstituted) using well-defined alkylidene complexes as initiators. Diethyl dipropargylmalonate (2a), di-tert-butyl dipropargylmalonate (2b), optically active di-(1R,2S,5R)-([minus])-menthyl dipropargylmalonate (2c([minus])), di-(1S,2R,5S)-(+)-menthyl dipropargylmalonate (2c(+)), di-(1R)-endo-(+)-fenchyl dipropargylmalonate (2d), 4,4-bis[[(p-tolylsulfonyl) oxy]methyl]-1,6-heptadiyne (3b), 4,4-bis[(trimethylsiloxy)methyl]-1,6-heptadiyne (3c), the cyclic silyl ether, PhEtSi(OCH[sub 2])[sub 2]C-(CH[sub 2]C[triple bond]CH)[sub 2] (3d), and N,N-dipropargyl-2,4,6-triisopropylbenzamide (5b) are polymerized to give soluble polymers in high yield using Mo(NAr)(CHCMe[sub 2]Ph)(OR[sub F6])[sub 2] (1a; Ar = 2,6-i-Pr[sub 2]C[sub 6]H[sub 3], OR[sub F6] = OCMe(CF[sub 3])[sub 2]) as the initiator in 1,2-dimethoxyethane (DME). The polymers show a high degree of conjugation ([lambda][sub max] > 500 nm) andmore »« less
https://doi.org/10.1021/ja00086a016
Synthesis of five- and six-coordinate alkylidene complexes of the type Mo(CHR)(NAr)[OCMe(CF[sub 3])[sub 2]][sub 2]S[sub x] and their use as living ROMP initiators or wittig reagents

Journal Article Fox, H H ; Lee, J K ; Park, L Y ; ... - Organometallics; (United States)

Addition of a slight excess of 4-methoxy-1-hexene to Mo(CHCMe[sub 2]Ph)(NAr)(OR[sub F6])[sub 2] (1a) or Mo(CHCMe[sub 3])(NAr)(OR[sub F6])[sub 2] (1b) in pentane (OR[sub F6] = OCMe(CF[sub 3])[sub 2]) yielded crystalline, red-orange anti-Mo[CHCH[sub 2]CH(OMe)CH[sub 2]CH[sub 3]](NAr)(OR[sub F6])[sub 2] (2). A similar reaction was used to prepare the difunctional complex anti-[(ArN)(OR[sub F6])[sub 2]Mo=CHCH[sub 2]CH(OMe)][sub 2]C[sub 6]H[sub 4] (3). Styrene reacts with 1a or 1b in DME over a period of 12 h to afford orange syn-Mo(CHPh)(NAr)-(OR[sub F6])[sub 2](DME) (4) in good yield. 4-(Dimethylamino)styrene and 2,4,6-trimethyoxystyrene react analogously to yield dark red syn-Mo(CH-4-C[sub 6]H[sub 4]-NMe[sub 2])(NAr)(OR[sub F6])[sub 2] (DME) (5) and red anti-Mo[CH-2,4,6-C[sub 6]H[submore »« less
https://doi.org/10.1021/om00027a028

Similar Records

Title: Stereoselective Ring-Opening Metathesis Polymerization (ROMP) of Methyl- N -(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate by Molybdenum and Tungsten Initiators

Abstract

Citation Formats

High Oxidation State Multiple Metal−Carbon Bonds journal, January 2002

Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts journal, October 2003

Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry journal, August 2009

Transition metal–carbon multiple bonds journal, January 2001

Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts † journal, March 2010

Synthesis of stereoregular ROMP polymers using molybdenum and tungsten imido alkylidene initiators journal, May 2011

Synthesis of Stereoregular Polymers through Ring-Opening Metathesis Polymerization journal, June 2014

Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide Complex journal, June 2009

Z-Selective and Syndioselective Ring-Opening Metathesis Polymerization (ROMP) Initiated by Monoaryloxidepyrrolide (MAP) Catalysts journal, September 2010

Synthesis of cis,syndiotactic ROMP Polymers Containing Alternating Enantiomers journal, January 2011

Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate journal, January 1990

Ring opening metathesis polymerization of methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate journal, January 1997

Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes journal, December 2011

Understanding d 0 -Olefin Metathesis Catalysts: Which Metal, Which Ligands? journal, July 2007

Inversion of Configuration at the Metal in Diastereomeric Imido Alkylidene Monoaryloxide Monopyrrolide Complexes of Molybdenum journal, January 2009

Fundamental Studies of Tungsten Alkylidene Imido Monoalkoxidepyrrolide Complexes journal, June 2009

Fundamental Studies of Molybdenum and Tungsten Methylidene and Metallacyclobutane Complexes † journal, November 2010

Stereomutation in Trigonal-Bipyramidal Systems: A Unified Picture journal, August 2011

Stereospecific Ring-Opening Metathesis Polymerization of Norbornadienes Employing Tungsten Oxo Alkylidene Initiators journal, July 2014

Synthesis of a poly(2-azanorbornene) with a high degree of cis-TT-stereoregularity and a regular secondary solution structure journal, January 2012

Bipyridine Adducts of Molybdenum Imido Alkylidene and Imido Alkylidyne Complexes journal, May 2012

Syntheses of Tungsten tert-Butylimido and Adamantylimido Alkylidene Complexes Employing Pyridinium Chloride As the Acid journal, August 2012

Molybdenum Imido Alkylidene Metathesis Catalysts That Contain Electron-Withdrawing Biphenolates or Binaphtholates journal, April 2007

Alkylidene and Metalacyclic Complexes of Tungsten that Contain a Chiral Biphenoxide Ligand. Synthesis, Asymmetric Ring-Closing Metathesis, and Mechanistic Investigations journal, March 2003

Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands journal, September 2014

Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis journal, November 2008

Functional Precision Polymers via Stereo- and Regioselective Polymerization Using Group 6 Metal Alkylidene and Group 6 and 8 Metal Alkylidene N -Heterocyclic Carbene Complexes journal, August 2018

High Oxidation State Multiple Metal−Carbon Bonds
journal, January 2002

Molybdenum and Tungsten Imido Alkylidene Complexes as Efficient Olefin-Metathesis Catalysts
journal, October 2003

Recent Advances in High Oxidation State Mo and W Imido Alkylidene Chemistry
journal, August 2009

Transition metal–carbon multiple bonds
journal, January 2001

Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts ^†
journal, March 2010

Synthesis of stereoregular ROMP polymers using molybdenum and tungsten imido alkylidene initiators
journal, May 2011

Synthesis of Stereoregular Polymers through Ring-Opening Metathesis Polymerization
journal, June 2014

Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide Complex
journal, June 2009

Z-Selective and Syndioselective Ring-Opening Metathesis Polymerization (ROMP) Initiated by Monoaryloxidepyrrolide (MAP) Catalysts
journal, September 2010

Synthesis of cis,syndiotactic ROMP Polymers Containing Alternating Enantiomers
journal, January 2011

Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate
journal, January 1990

Ring opening metathesis polymerization of methyl-N-(1-phenylethyl)-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate
journal, January 1997

Z-Selective Olefin Metathesis Reactions Promoted by Tungsten Oxo Alkylidene Complexes
journal, December 2011

Understanding d ⁰ -Olefin Metathesis Catalysts: Which Metal, Which Ligands?
journal, July 2007

Inversion of Configuration at the Metal in Diastereomeric Imido Alkylidene Monoaryloxide Monopyrrolide Complexes of Molybdenum
journal, January 2009

Fundamental Studies of Tungsten Alkylidene Imido Monoalkoxidepyrrolide Complexes
journal, June 2009

Fundamental Studies of Molybdenum and Tungsten Methylidene and Metallacyclobutane Complexes ^†
journal, November 2010

Stereomutation in Trigonal-Bipyramidal Systems: A Unified Picture
journal, August 2011

Stereospecific Ring-Opening Metathesis Polymerization of Norbornadienes Employing Tungsten Oxo Alkylidene Initiators
journal, July 2014

Synthesis of a poly(2-azanorbornene) with a high degree of cis-TT-stereoregularity and a regular secondary solution structure
journal, January 2012

Bipyridine Adducts of Molybdenum Imido Alkylidene and Imido Alkylidyne Complexes
journal, May 2012

Syntheses of Tungsten tert-Butylimido and Adamantylimido Alkylidene Complexes Employing Pyridinium Chloride As the Acid
journal, August 2012

Molybdenum Imido Alkylidene Metathesis Catalysts That Contain Electron-Withdrawing Biphenolates or Binaphtholates
journal, April 2007

Alkylidene and Metalacyclic Complexes of Tungsten that Contain a Chiral Biphenoxide Ligand. Synthesis, Asymmetric Ring-Closing Metathesis, and Mechanistic Investigations
journal, March 2003

Synthesis of Molybdenum and Tungsten Alkylidene Complexes That Contain Sterically Demanding Arenethiolate Ligands
journal, September 2014

Highly efficient molybdenum-based catalysts for enantioselective alkene metathesis
journal, November 2008

Functional Precision Polymers via Stereo- and Regioselective Polymerization Using Group 6 Metal Alkylidene and Group 6 and 8 Metal Alkylidene N -Heterocyclic Carbene Complexes
journal, August 2018