Insight into 6π Electrocyclic Reactions of 1,8-Dioxatetraene

Xiaodong Si; Yuanyuan Jia; Xinqi Luan; Luo Yang; Yong Pei; Wang Zhou

doi:10.1002/anie.201812090

Insight into 6π Electrocyclic Reactions of 1,8-Dioxatetraene

Angew Chem Int Ed Engl. 2019 Feb 25;58(9):2660-2664. doi: 10.1002/anie.201812090. Epub 2019 Jan 29.

Authors

Xiaodong Si^{1

2}, Yuanyuan Jia^{1

2}, Xinqi Luan³, Luo Yang³, Yong Pei³, Wang Zhou^{1

2

3}

Affiliations

¹ College of Chemical Engineering, Xiangtan University, Hunan, 411105, China.
² State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Xue Yuan Road 38, Beijing, 100191, China.
³ Key Laboratory for Green Organic Synthesis and Application of Hunan Province, College of Chemistry, Xiangtan University, Hunan, 411105, China.

PMID: 30600881
DOI: 10.1002/anie.201812090

Abstract

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.

Keywords: electrocyclizations; photochromic compound; reaction mechanisms; rhodium; spiro-compounds.

Abstract

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