1969 年 89 巻 12 号 p. 1631-1636
Bordwell, et al.8) had reported that DL-trans-2-p-tolylthiocyclohexyl S-methyl xanthate (IX) suffered cis-elimination by the Chugaev reaction. However, the present study revealed that the analogue (Ia) carrying a methylthio group in place of the tolylthio group in IX underwent rearrangement to the corresponding dithiolcarbonate. The rearrangement of Ia was attributed to the anchimeric power of the methylthio group. A variety of 2-methylthioalkyl S-methyl xanthates and DL-trans-2-methylthiocyclohexyl N, N-dimethylthionocarbamate (Ib) were thermally treated and the results provided evidences for this rearrangement mechanism which was analogous to that proposed in the case of 2-dialkylaminoalkyl S-methyl xanthates.