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- W2024007095 abstract "Treatment of solutions of 1,3-thiazole-5(4H)-thiones 1 in CH2Cl2 at room temperature with BF3⋅Et2O and 1,2-epoxycyclohexane (7-oxabicyclo[4.1.0]heptane; 2a) or 1,2-epoxycyclopentane (6-oxabicyclo[3.1.0]hexane; 2b) yielded mixtures of diastereoisomeric spirocyclic 1,3-oxathiolanes (3/4 and 8/9, respectively). In addition, the corresponding 1,3-dithiolane 6 was formed as a minor product in the reaction of 4,4-dimethyl-2-phenyl-1,3-thiazole-5(4H)-thione (1a) with 2a. The structures of the different types of products have been established by X-ray crystal-structure analysis. An ionic two-step mechanism via nucleophilic ring-opening of the complexed oxirane by the attack of the thiocarbonyl S-atom is proposed. This proposal is supported by the formation of the propellane 10 with a Wagner-Meerwein rearrangement as the key step." @default.
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- W2024007095 date "1999-09-08" @default.
- W2024007095 modified "2023-09-23" @default.
- W2024007095 title "Reaction of 1,3-Thiazole-5(4H)-thiones with 1,2-Epoxycycloalkanes: Formation of Spirocyclic 1,3-Oxathiolanes" @default.
- W2024007095 doi "https://doi.org/10.1002/(sici)1522-2675(19990908)82:9<1458::aid-hlca1458>3.0.co;2-g" @default.
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