Ring-opening Reaction of Oxiranes, Oxetanes, and Tetrahydropyran by Mercury(II) Salts and Alkyl Halides
作者:Nanao Watanabe、Sakae Uemura、Masaya Okano
DOI:10.1246/bcsj.52.3611
日期:1979.12
The reaction of primary and secondary alkyl halides with mercury(II) acetate in oxiranes, oxetanes, and tetrahydropyran results in ring-opening to give the corresponding alkoxyalkyl acetates. Similar reactions with mercury(II) thiocyanate in oxetanes afford alkoxyalkyl isothiocyanate and thiocyanate, ROCH2C(R′)2CH2NCS and ROCH2C(R′)2CH2SCN, where the isomer ratios (N/S ratios) are 82–96/4–18. It is
伯和仲烷基卤化物与乙酸汞 (II) 在环氧乙烷、氧杂环丁烷和四氢吡喃中的反应导致开环,得到相应的烷氧基烷基乙酸酯。与氧杂环丁烷中硫氰酸汞 (II) 的类似反应得到烷氧基烷基异硫氰酸酯和硫氰酸酯、ROCH2C(R')2CH2NCS 和 ROCH2C(R')2CH2SCN,其中异构体比率(N/S 比率)为 82-96/4-18。这表明反应涉及三元、四元或六元 O-烷基氧鎓离子中间体的初始形成和随后的 XHgZ2- 攻击。