PHOTOHYDRATION REACTION OF 1-(p-NITROPHENYL)-5,5-DIMETHYL-1,3-HEXADIYNE

Article abstract of DOI:10.1002/poc.610081102

Irradiation of 1-(p-nitrophenyl)-5,5-dimethyl-1,3-hexadiyne (NDHD) in aqueous sulfuric acid yields conjugated allenyl ketones (1 and 2) and β-dicarbonyl compounds (3 and 4).The products 1 and 2 are primary photoproducts while 3 and 4 are secondary products formed by thermal hydration of the primary photoproducts showing the maximum quantum yield at H₀=-1.0.A mechanism involving a synchronous addition of hydronium ion (H3O(1+)) to a triplet state of NDHD is proposed.