CYANO SUBSTITUTED OZONIDES - PREPARATION, PROPERTIES AND UNUSUAL BEHAVIOR TOWARDS REDUCING AGENTS

Ozonolyses of 2-cyanopropene (1a) and of 2,4-dicyano-1-butene (1b) gave the corresponding ozonides 3-cyano-3-methyl-(2a) and 3-cyano-3-(2-cyanoethyl)-1,2,4-trioxolane (2b) as the first examples of their kind. Reduction with DMS yielded the expected fragments acetyl cyanide (4a) and β-cyanopropionyl cyanide (4b), along with fomaldehyde. Reduction with triphenylphosphine, however, gave cyanomethyl acetate (6a) and cyanomethyl-β-cyanopropionate (6b), respectively. © 1990.