Tetrahedron Letters p. 3299 - 3300 (1990)
Update date:2022-07-29
Topics:
Griesbaum, Karl
Huh, Tae-Seong
Gutsche, Sven-Hendrik
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 formaldehyde.Reduction with triphenylphosphine, however, gave cyanomethyl acetate (6a) and cyanomethyl-β-cyanopropionate (6b), respectively.
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