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Alkyl‐Group Selection in an Acidic‐Surfactant‐Promoted Reaction of Homoallyl Alcohols and Aldehydes in Water
Author(s) -
Hatakeyama Takanori,
Chisaka Yuki,
Kuroda Chiaki
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200800434
Subject(s) - chemistry , aldehyde , alkyl , pulmonary surfactant , alcohol , substituent , aqueous solution , organic chemistry , sodium dodecyl sulfate , medicinal chemistry , catalysis , biochemistry
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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