HINDERED ORGANOBORON GROUPS IN ORGANIC-CHEMISTRY .24. THE CONDENSATION OF ALIPHATIC-ALDEHYDES WITH DIMESITYLBORON STABILIZED CARBANIONS TO GIVE KETONES

Authors
PELTER A SMITH K ELGENDY SMA ROWLANDS M
Citation
A. Pelter et al., HINDERED ORGANOBORON GROUPS IN ORGANIC-CHEMISTRY .24. THE CONDENSATION OF ALIPHATIC-ALDEHYDES WITH DIMESITYLBORON STABILIZED CARBANIONS TO GIVE KETONES, Tetrahedron, 49(32), 1993, pp. 7104-7118
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
49
Issue
32
Year of publication
1993
Pages
7104 - 7118
Database
ISI
SICI code
0040-4020(1993)49:32<7104:HOGIO.>2.0.ZU;2-I
Abstract
The condensation of boron stabilised carbanions, Mes2BCHLiR1, (R1 not- equal H) with aliphatic aldehydes, R2CHO, followed by treatment with t rifluoroacetic anhydride (TFAA) or N-chlorosuccinimide (NCS) is an uni que, 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.