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Synthesis 2005(15): 2623-2624  
DOI: 10.1055/s-2005-872115
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Aqueous Solvents Dictate the Regiochemistry in the Photooxidations of α,β-Unsaturated Carboxylic Acid Salts

Kristina L. Stensaas*, Anisha Bajaj
Department of Chemistry, Millsaps College, 1701 North State Street, Jackson, MS 39210, USA
Fax: +1(601)9741401; e-Mail: stenskl@millsaps.edu;
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Publication History

Received 14 June 2005
Publication Date:
05 August 2005 (online)

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Abstract

Aqueous singlet oxygen photooxidations of the sodium salts of angelic acid, tiglic acid, and 2,3-dimethyl-2-butenoic acid were conducted. Each reaction produced an overwhelming amount of the ene hydroperoxide resulting from hydrogen abstraction geminal to the electron withdrawing group. The resulting regiochemistry is insensitive to the alkyl substitution on the substrate.

Key words

carboxylic acid salts - aqueous reactions - photooxidation - singlet oxygen ene reaction - allylic alcohol