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Updated: Oct 10, 2025

Preparation and Use of Carbonyl-decorated Carbenes in the Activation of White Phosphorus
Published on: October 3, 2014
8π Electrocyclic Reaction of Phosphonate Derivatives: Access to Seven-Membered Cross-Conjugated Cyclic Trienes
Hiroki Saito1, Ranmaru Kato1, Kazutada Ikeuchi2
1Graduate School of Chemical Sciences and Engineering, Hokkaido University, Sapporo 060-0810, Japan.
Abstract:
An anionic 8π electrocyclic reaction of 4-(diethoxyphosphoryl)-1,3,6-heptatriene derivatives was developed. Under the influence of a base, the substrate underwent deprotonation at the C5 position followed by the 8π electrocyclization of the resulting heptatrienyl anion. The subsequent Horner-Wadsworth-Emmons reaction in one pot, following the addition of an aldehyde, resulted in the production of the 3-alkylidene-1,4-cycloheptadiene derivative. The electrocyclic reaction proceeded in a stereospecific manner, resulting in the stereocontrolled formation of two neighboring stereogenic centers.
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