Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones

Pelter, Andrew, Smith, Keith, Elgendy, Said M. A. and Rowlands, Martin 1993. Hindered organoboron groups in organic chemistry. 24. The condensation of aliphatic aldehydes with dimesitylboron stabilised carbanions to give ketones. Tetrahedron 49 (32) , pp. 7104-7118. 10.1016/S0040-4020(01)87982-5

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Abstract

The condensation of boron stabilised carbanions, Mes2BCHLiR1, (R1≠H) with aliphatic aldehydes, R2CHO, followed by treatment with trifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an unique, broadly applicable redox process that yields ketones, R1CH2COR2, directly and in high yields. The anion Mes2BCH2Li (Mes2BCHLiR1, R1H) gives high yields of alkenes, R2CHCH2 in the same conditions.

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:	https://orca.cardiff.ac.uk/id/eprint/12672

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