Ring-opening reaction of oxiranes, oxetanes, and tetrahydropyran by mercury (II) salts and alkyl halides.

N Watanabe, S Uemura, M Okano

Index: Watanabe,N. et al. Bulletin of the Chemical Society of Japan, 1979 , vol. 52, p. 3611 - 3614

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Citation Number: 2

Abstract

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, ROCH 2 C (R′) 2 CH 2 NCS and ROCH 2 C (R′) 2 CH 2 SCN, where the isomer ratios (N/S ratios) are 82–96/4–18. It is suggested that the ...