Polyenes Communication 4. Synthesis of aryl polyenic hydrocarbons with the aid of organometallic compounds

Research paper by B. M. Mikhailov, G. S. Ter-Sarkisyan, F. B. Tutorskaya

Indexed on: 01 May '59Published on: 01 May '59Published in: Russian Chemical Bulletin


Benzylsodium undergoes 1,2-addition to cinnamaldehyde and β-methylcinnamaldehyde and also to those unsaturated ketones in which there is a methyl group adjacent to the carbonyl group. On the other hand, the addition of benzylsodium to 5-phenyl-2,4-pentadienophenone occurs in the 1,4-position, whereas this ketone reacts with 2-pyridylrnethyllithium in the 1,2-position.Phenyllithium reacts with 4-phenyl-3-buten-2-one and with 6-phenyl-3,5-hexadien-2-one with formation of alcohols, the dehydration of which results in the formation of dimers of the corresponding hydrocarbons.Some new polyenic compounds were synthesized.