Volume 24, Issue 14
Preparative Organic Chemistry
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ChemInform Abstract: Flash Photolytic Generation and Reactivity of Phenyl(methylthio)ketene in Aqueous Solution.

J. JUN. JONES

J. JUN. JONES

Dep. Chem., Univ. Toronto, Ontario M5S 1A1, Can.

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A. J. KRESGE

A. J. KRESGE

Dep. Chem., Univ. Toronto, Ontario M5S 1A1, Can.

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First published: April 6, 1993

Abstract

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ChemInform Abstract

Flash photolysis of S-methyl diazophenylthioacetate (I) at neutral, acidic, or basic conditions yields α-(methythio)phenylacetic acid (II) as the only product. The mechanism involves a rearrangement of a carbene to generate (methylthio)phenylketene which undergoes addition of water to give (II).

chemical structure image

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