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Organic Chemistry

Reaction of MTBO with Alcohols

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Pages 115-121 | Received 26 Jun 1972, Published online: 09 Sep 2014
 

Abstract

A new phosphorylating agent, 2-methylthio-4H-1,3,2-benzodioxaphosphorin-2-oxide (MTBO), prepared from its thiono isomer, 2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-sulfide (MOBS), by means of the Pistschimuka reaction, reacted with several aliphatic alcohols in the presence of cyclohexylamine to give the corresponding O-alkyl S-methyl phosphorothiolates in 60 to 45% yield.

The phosphorothiolates could be converted to phosphate diesters as well as monoesters by the action of an oxidizing agent such as isoamyl nitrite or iodine in dry alcohol or in water.

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