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Alkyl-Group Selection in an Acidic-Surfactant-Promoted Reaction of Homoallyl Alcohols and Aldehydes in Water

✍ Scribed by Takanori Hatakeyama; Yuki Chisaka; Chiaki Kuroda

Publisher
John Wiley and Sons
Year
2009
Tongue
German
Weight
172 KB
Volume
92
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The hydrophobic effect in the reaction of a homoallyl alcohol with an aldehyde (Yadav's reaction system) under aqueous conditions in the presence of an acidic surfactant was studied indicating the presence of the alkyl‐substituent effect, although not a dramatic one. The DBSA‐promoted reaction proceeds relatively faster when both the homoallyl alcohol and the aldehyde carry a cycloalkyl group (DBSA=4‐dodecylbenzenesulfonic acid). In contrast, the reaction of the substrates having an unbranched alkyl group is relatively more favorable in SDS/HCl than in DBSA (SDS=sodium dodecyl sulfate).

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