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Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes

Pelter, Andrew, Smith, Keith and Elgendy, Said M. A. 1993. Hindered organoboron groups in organic chemistry. 25. The condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions to give alkenes. Tetrahedron 49 (32) , pp. 7119-7132. 10.1016/S0040-4020(01)87983-7

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Abstract

In the presence of protic acids the condensation of aliphatic aldehydes with dimesitylboryl stabilised carbanions results in alkenes. In the presence of strong acids such as HCl or CF3SO3H, the products contain > 90% of E-alkenes in all cases tried. When acetic acid is used, then Z-alkenes may result predominantly, particularly in the cases of RsCHO and RtCHO. HX  HCI, CF3SO3H gives E - alkenes in all cases. HX  CH3CO2H gives mainly Z - alkenes when R  Rsec, Rtert.

Item Type: Article
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: Pergamon Press
ISSN: 0040-4020
Last Modified: 04 Jun 2017 02:51
URI: http://orca.cf.ac.uk/id/eprint/12671

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