Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination
Thermal conversion of primary alcohols to disulfides via xanthate intermediates: an extension to the Chugaev elimination
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通过黄原酸盐中间体将伯醇热转化为二硫化物：Chugaev 消除法的延伸
DOI：
10.1039/c8ob00024g
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发表时间：
2018
影响因子：
3.2
通讯作者：
Xu Jiaxi
中科院分区：
文献类型：
--
作者：
He Wei;Ding Yong;Tu Jianzhuo;Que Chuqiang;Yang Zhanhui;Xu Jiaxi
伯醇通过加热原位生成O-烷基S-二氟（乙氧羰基）甲基黄原酸酯转化为二烷基二硫化物，所述O-烷基S-二氟（乙氧羰基）甲基黄原酸酯由溴二氟乙酸乙酯和黄原酸钾在KOH存在下由伯醇和二硫化碳制备。反应机理建议为烷基C[1，3]移位，然后是自由基机理。这延伸到产生烯烃的Chugaev消除。目前的研究提供了从市售伯烷醇容易地获得二烷基二硫化物。
Primary alcohols are converted into dialkyl disulfides via heating in situ generated O-alkyl S-difluoro(ethoxycarbonyl)methyl xanthates from ethyl bromodifluoroacetate and potassium xanthates, prepared from primary alcohols and carbon disulfide in the presence of KOH. The reaction mechanism is suggested as an alkyl C[1,3] shift followed by a radical mechanism. This extends to the Chugaev elimination which yields olefins. The current research provides easy access to dialkyl disulfides from commercially available primary alkanols.