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Insight into 6π Electrocyclic Reactions of 1,8‐Dioxatetraene
Author(s) -
Si Xiaodong,
Jia Yuanyuan,
Luan Xinqi,
Yang Luo,
Pei Yong,
Zhou Wang
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201812090
Subject(s) - steric effects , electrocyclic reaction , photochromism , reactivity (psychology) , chemistry , computational chemistry , photochemistry , stereochemistry , bicyclic molecule , medicine , alternative medicine , pathology
A variety of benzofuranone‐based spiroisochromenes were originally designed and synthesized to gain insight into the oxa‐6π electrocyclic reaction of cis , cis ‐1,8‐dioxatetraene for the first time. The stability of the 1,8‐dioxatetraene intermediate is governed by its steric congestion and can be fine‐tuned through modification of the backbone structure, leading to the reactivity differences in the 6π electrocyclic reaction and the emergence of photochromic properties.