Title: Facile Insertion of Ethylene into a Group 14 Element-Carbon Bond: Effects of the HOMO-LUMO Energy Gap on Reactivity

Journal Article · · ChemComm
DOI: https://doi.org/10.1039/c8cc08488b · OSTI ID:1609927
 [1];  [2]; ORCiD logo [3]; ORCiD logo [2]; ORCiD logo [3]
  1. Univ. of California, Davis, CA (United States); DOE/OSTI
  2. Kyoto Univ. (Japan)
  3. Univ. of California, Davis, CA (United States)
+ Show Author Affiliations

The diarylstannylenes, Sn(AriPr4)2 and Sn(AriPr6)2, (AriPr4 = C6H3-2,6-(C6H3-2,6-iPr2)2, AriPr6 = C6H3-2,6-(C6H2-2,4,6-iPr3)2), undergo a facile migratory insertion reaction with ethylene at 60 °C to afford the alkyl aryl stannylenes AriPr4SnCH2CH2AriPr4 and AriPr6SnCH2CH2AriPr6 which were characterized via1H, 13C and 119Sn NMR, UV-vis and IR spectroscopy, as well as by X-ray crystallography. In this work, quantum mechanical calculations were performed, and two potential mechanisms were identified, with a migratory insertion reaction pathyway being energetically preferred.

Research Organization:
Univ. of California, Davis, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
FG02-07ER46475
OSTI ID:
1609927
Journal Information:
ChemComm, Journal Name: ChemComm Journal Issue: 3 Vol. 55; ISSN CHCOFS; ISSN 1359-7345
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

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Cited By (2)

Carbon monoxide insertion at a heavy p-block element: unprecedented formation of a cationic bismuth carbamoyl journal January 2019
1,2-Insertion reactions of alkynes into Ge–C bonds of arylbromogermylene journal January 2020

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