Alkyl‐Group Selection in an Acidic‐Surfactant‐Promoted Reaction of Homoallyl Alcohols and Aldehydes in Water |
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| Authors: | Takanori Hatakeyama Yuki Chisaka Chiaki Kuroda |
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| Institution: | 1. Department of Chemistry, Rikkyo University, Nishi‐Ikebukuro, Toshima‐ku, Tokyo 171‐8501, Japan;2. Research Center for Smart Molecules, Rikkyo University, Nishi‐Ikebukuro, Toshima‐ku, Tokyo 171‐8501, Japan (phone/fax: +81‐339852396) |
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| 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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| Keywords: | Homoallyl alcohols Cyclization reactions Surfactants Hydrophobic effect |
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