Thermal transformations of allyl 2-thienyl sulfide and selenide
✍ Scribed by N. A. Korchevin; É. N. Sukhomazova; N. V. Russavskaya; L. P. Turchaninova; M. V. Sigalov; L. V. Klyba; É. N. Deryagina; M. G. Voronkov
- Publisher
- Springer US
- Year
- 1991
- Tongue
- English
- Weight
- 349 KB
- Volume
- 27
- Category
- Article
- ISSN
- 0009-3122
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✦ Synopsis
In the gas phase at 350-410~ allyl 2-thienyl sulfide is converted to thiophene-2-thiol, di(2-thienyl) sulfide, and 2-methylthieno[2,3-b]thiophene. In the presence of acetylene thieno [2,3-b]thiophene is formed in addition to these products. Allyl 2-thienyl selenide is converted quantitatively to 2,3dihydro-2-methylselenopheno [2,3-b]thiophene during fractional distillation in vacuo. Thiophene, di(2-thienyl) selenide, di(2-thienyl) diselenide, thiophene-2-selenol, and 2-methylselenopheno/2,3b]thiophene are formed in addition to these compounds in the thermolysis of allyl thienyl selenide in the gas. phase. In the presence of acetylene the thermal decomposition of allyl thienyl selenide is accompanied by the formation of selenophene.
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The electron impact (EI) mass spectra of allyl aryl selenides showed abundant molecular ions and many fragment ions containing the selenium atom. a-Cleavage is the dominant process in the fragmentation of selenides, and cleavage product ions are characteristic of the substituents. In the case of 3-m
## Abstract An efficient and mild reaction for introducing an allylic moiety and an alkylthio‐ or alkylseleno‐group onto the α‐carbon of β‐dicarbonyl compounds in one step by tandem transylidation and [2,3]‐sigmatropic rearrangement is described.