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Synthesis and Photochemistry of 2,2‐Dimethyl‐3(2 H )‐thiophenone, a Ketonic Tautomer of 3‐Hydroxythiophene. Preliminary Communication
Author(s) -
Anklam Elke,
GhaffariTabrizi Ramin,
Hombrecher Hermann,
Lau Sabine,
Margaretha Paul
Publication year - 1984
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.19840670528
Subject(s) - chemistry , cyclopentenone , tautomer , cycloaddition , cyclobutane , enone , photochemistry , keto–enol tautomerism , stereospecificity , medicinal chemistry , ionone , stereochemistry , organic chemistry , catalysis , ring (chemistry)
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.