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Insertion of two CO moieties into an alkene double bond to form a RCH = C(O)C(O) = CHR/sup 2 -/ unit via organosamarium activation

Journal Article · · J. Am. Chem. Soc.; (United States)
DOI:https://doi.org/10.1021/ja00217a013· OSTI ID:7076899
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RCH=CHR (R = 2-pyridyl) reacts with (C/sub 5/Me/sub 5/)/sub 2/Sm(THF)/sub 2/ to form a red complex, which reacts with CO at 80 psi in toluene to form ((C/sub 5/Me/sub 5/)/sub 2/Sm)/sub 2/(..mu..-eta/sup 4/-RCH=C(O)C(O)=CHR) (1) in 90% yield. 1 cocrystallizes with 2 molecules of toluene in space group C2/m with a = 15.818 (2) A, b = 14.060 (2) A, c = 15.353 (2) A, ..beta.. = 111.480 (12)/sup 0/, and Z = 2 for D/sub calcd/ = 1.32 g cm/sup -3/. Least-squares refinement on the basis of 2526 observed reflections led to a final R value of 0.045. The two (C/sub 5/Me/sub 5/)/sub 2/Sm units are bridged by a tetradentate bisenolate ligand, RCH=C(O)C(O)=CHR/sup 2 -/, such that each Sm is coordinated to one oxygen and the nitrogen atom of the pyridyl group closest to that oxygen. The Sm-O, Sm-N, and average Sm-C(ring) distances are 2.191 (6), 2.473 (7), and 2.71 (1) A, respectively.

Research Organization:
Univ. of California, Irvine (USA)
OSTI ID:
7076899
Journal Information:
J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 110:9; ISSN JACSA
Country of Publication:
United States
Language:
English

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ALKENES
CARBONYLS
CHEMICAL BONDS
CHEMICAL PREPARATION
CHEMICAL REACTIONS
CRYSTAL STRUCTURE
DATA
DOUBLE BONDS
EXPERIMENTAL DATA
HYDROCARBONS
INFORMATION
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANOMETALLIC COMPOUNDS
RARE EARTH COMPOUNDS
SAMARIUM COMPOUNDS
SPACE GROUPS
SYNTHESIS