Reaction of Aromatic Thiocyanates with Trialkyl Phosphites
K Pilgram, DD Phillips
Index: Pilgram,K.; Phillips,D.D. Journal of Organic Chemistry, 1965 , vol. 30, p. 2388 - 2392
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Citation Number: 17
Abstract
In contrast to aliphatic thiocyanates, which react with trialkyl phosphites exclusively by an Arbuzov mechanism to form phosphorothioates, aromatic thiocyanates, ArSCN, react with trialkyl phosphites,(RO) 3P, to give a mixture of phosphorothioate and sulfide, RSAr. The formation of sulfide is favored by substituents (NO?, etc.) on the aryl ring that can stabilize an anionic species, an observation that suggests a mechanism involving attack of phosphite ...
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