Recueil des Travaux Chimiques des Pays-Bas p. 92 - 98 (1992)
Update date:2022-08-02
Topics:
Groesbeek, M.
Robijn, G. W.
Lugtenburg, J.
7E,13E-11,19-10,20-dimethanoretinal (1) and its 13Z isomer 2 were prepared from β-ionone, using the novel synthon 2-(diethoxyphosphinyl)-5,5-dimethoxyhexanenitrile.This synthon was also used to prepare 7E,9E,13E-10,20-methanoretinal (3) and its 13Z isomer 4 in high yield, starting from β-ionone.Spectroscopic analysis (mass, 1H and 13C NMR and UV/Vis) of these compounds is discussed.The introduction of the methano bridges leads to minimal steric and electronic changes.The photostationary state reached from 1 and 2 has the 13Z form 2 as the main constituent.This is one of the very few with a Z form as the main constituent of the photostationary state. 1 and 2 are very sensitive to acid-catalyzed isomerization of the 13-C=14-C double bond.The presence of the 11,19-methano bridge is responsible for this efficient Z-E isomerization.
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