Rearrangement and trans-Elimination contrary to the Chugaev Reaction Rule. IX. Thermal Rearrangement of 2-Cycloalkenyl S-Alkyl Xanthate

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概要

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• S-Methyl xanthates of 2-cyclohexen-1-ol (IV), 3-methyl-2-cyclohexen-1-ol (V) and cis-3,5-dimethyl-2-cyclohexen-1-ol (VI) transformed to dithiolcarbonates (VIII, IX and X) accompanying allylic shift (S_<Ni'>). On the other hand, S-methyl xanthate of 3,5,5-trimethyl-2-cyclohexen-1-ol (VII) transformed to 3,5,5-trimethyl-2-cyclohexenyl methyl dithiolcarbonate (XI), without allylic shift (S_<Ni>). Of polycyclic system, S-methyl xanthates of ⊿^<1,9>-octalin-2-ol (XIII) and ⊿^4-cholesten-3β-ol (XIX) were submitted to pyrolysis and consequently it was found that they decomposed into methylthio derivatives (XVI and XXI) via rearragement to the dithiolcarbonates (XV and XX). In homoallylic system, pyrolysis of S-alkyl xanthates of cholesterol in the presence of phenolic solvent caused the rearrangement to the corresponding dithiolcarbonates with retention of configuration. In each rearrangement reaction, reaction courses are discussed.

• 公益社団法人日本薬学会の論文
• 1972-11-25

著者

• 原野 一誠

  Faculty of Pharmaceutical Sciences, Kumamoto University

• 原野 一誠

  崇城大学薬学部

• 田口 胤三

  Faculty of Pharmaceutical Sciences, Kyushu University

• 田口 胤三

  Faculty Of Pharmaceutical Sciences Kyushu University

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