74 nitrosyl chloride, reaction with aldehydes

Substitutedisoxazole-3,5-dicarboxylic acids have been prepared from ethyl nitroacetate and an aldehyde (63BCJii50). A related reaction leads to diethyl 4-hydroxyisoxazole-3,5-dicarboxylate (334) and involves the reaction of acetonedicarboxylic acid ester (333) with nitrosyl chloride (78JHC1519). 

The reaction of phosphine with aliphatic aldehydes is a useful method of C-P bond formation Dialkyl phosphites are smoothly converted to pyrophosphates with nitrosyl chloride . 2-Cyanoethyl phosphate has been introduced as a phosphorylating agent in the nucleotide field. The cyanoethyl group can be removed under mild alkaline conditions, which do not affect the essential part of the nucleotide . 

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