Selenophen-2-yl-Substituted Thiocarbonyl Ylides - at the Borderline of Dipolar and Biradical Reactivity
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منابع مشابه
Selenophen - 2 - yl - substituted thiocarbonyl ylides – at the borderline of dipolar and biradical reactivity
The reactions of aryl (selenophen-2-yl) thioketones with CH2N2 occur with spontaneous elimination of N2, even at low temperature (-65°), to give regioselectively sterically crowded 4,4,5,5tetrasubstituted 1,3-dithiolanes and/or a novel type of twelve-membered dithia-diselena heterocycles as dimers of the transient thiocarbonyl S-methanides. The ratio of these products depends on the type of sub...
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An intriguing stepwise diradical mechanism of the dimerization of the reactive intermediate (thiocarbonyl S-methanide) appearing in the reaction of phenyl selenophen-2-yl thioketone with diazomethane was studied by means of computational methods. The preferred formation of the unusual macroheterocycle, competitive with the 1,3-ring closure leading to a thiirane and the head-to-head dimerization...
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ژورنال
عنوان ژورنال: Helvetica Chimica Acta
سال: 2015
ISSN: 0018-019X
DOI: 10.1002/hlca.201500050