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Synthesis and Photochemistry of 2,2-Dimethyl-3(2H)-thiophenone, a Ketonic Tautomer of 3-Hydroxythiophene. Preliminary Communication

✍ Scribed by Elke Anklam; Ramin Ghaffari-Tabrizi; Hermann Hombrecher; Sabine Lau; Paul Margaretha

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
188 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

On irradiation (λ = 366 nm), the 4‐thia‐2‐cyclopentenone 3a behaves in complete analogy to the oxa‐enone 3c undergoing regio‐ and stereospecific cyclodimerization, regiospecific cycloaddition with 2‐methylpropene and cycloaddition with 2,3‐dimethyl‐2‐butene to afford cyclobutane derivatives. In contrast, the 4‐aza‐2‐cyclopentenone 3b does not undergo the above‐mentioned reactions but only slow photodecomposition.

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