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Convenient and efficient procedures for thiirans have been developed via a one-pot reaction of benzoxazolyl β-ketosulfides with NaBH 4 and NaOH in MeOH and THF. The reaction is considered to proceed via the spiro intermediate by the ipso-addition of β-hydroxygroup, which is formed by the NaBH 4 reduction of β-keto group, to 2-position of benzoxazole group.
Thermolyses of β-hydroxysulfides 2, bearing groups, such as 2-benzothiazolyl and 4-(4-methyl)-4H-1,2,4-triazolyl groups, were studied and found to afford the corresponding substituted styrenes 5 and hydroxy heteroaromatics in good yields, respectively. The product distribution change in the course of the thermolysis of 2a was also studied. The olefin products 5a were considered to be formed by the...
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