1981
DOI: 10.1016/s0040-4039(01)82973-7
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Photochemistry of bicyclic δ-thia-α,β-unsaturated ketones a vinylketene mechanism

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1982
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Cited by 12 publications
(4 citation statements)
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“…Similar light-induced 6 -4 ring contractions for S-heterocycles had been observed in studies on the photochemistry of isothiochroman-4-one [3] [4] and bicyclic S-thia-a,P-unsaturated ketones [5] [6]. In this latter study, the authors proposed that the formal 1,3-S migration might occur via a vinylketene intermediate, but no further mechanistic details were discussed.…”
supporting
confidence: 58%
“…Similar light-induced 6 -4 ring contractions for S-heterocycles had been observed in studies on the photochemistry of isothiochroman-4-one [3] [4] and bicyclic S-thia-a,P-unsaturated ketones [5] [6]. In this latter study, the authors proposed that the formal 1,3-S migration might occur via a vinylketene intermediate, but no further mechanistic details were discussed.…”
supporting
confidence: 58%
“…The photolysis of the δ-thia-α,β-unsaturated ketone 328 resulted in the formation of thietan-3-one 330 . , The overall reaction consisted of a 1,3-migration of the sulfur atom. Further evidence was supplied that the reaction took place via a [2+2]-cycloaddition of the vinylketene intermediate 329 …”
Section: A2 Synthesis By Ring Transformationsmentioning
confidence: 99%
“…Further evidence was supplied that the reaction took place via a [2+2]cycloaddition of the vinylketene intermediate 329. 230 Reaction of cyclic disulfides with carbenes, generated from catalytic or photochemical decomposition of diazo compounds, resulted in the formation of tetrasubstituted thietan-3-ones (Scheme 89, Table 5). 232 The products 332 resulted from S-S insertion of the disulfide and subsequent desulfurization.…”
Section: A2 Synthesis By Ring Transformationsmentioning
confidence: 99%
“…A strategy toward synthesis of benzo­[ b ]­thiophenes via tandem thien- and benz-annulations of simple acyclic precursors is an appealing alternative but has not been developed. To the best of our knowledge, up to now, there has been only one single example reported by Mukai wherein pyrolysis of bicyclic δ-thia-α,β-unsaturated ketone at 520 °C afforded 4-hydroxybenzo­[ b ]­thiophene in 28% yield . Although it remains unexploited, this strategy would be highly desirable because it would avoid using prefunctional aromatic ring substrates and the functional groups could be directly introduced onto the benzo­[ b ]­thiophene skeletons by choosing appropriate substrates.…”
mentioning
confidence: 99%