Open AccessPhotoelectrocyclization Reactions of Conjugated Cycloalkenones: Scope and Reactivity
Author(s) -
Xuchen Zhao,
Changqing Song,
Jon D. Rainier
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c00197
Subject(s) - conjugated system , scope (computer science) , reactivity (psychology) , hydride , singlet state , chemistry , aryl , substitution (logic) , combinatorial chemistry , photochemistry , excited state , organic chemistry , computer science , hydrogen , physics , medicine , alternative medicine , alkyl , pathology , nuclear physics , programming language , polymer
Outlined here are studies exploring the scope of the sequential photoelectrocyclization, [1,5]-hydride shift of conjugated bis-aryl cycloalkenone substrates. We have found not only that the cyclization precursors can be synthesized in a modular fashion but also that the cyclization is efficient and amenable to the presence of a range of cycloalkenones and aromatic systems. Among the interesting discoveries from this work is that the electrocyclization intermediate can be competitively captured with protons and that the nature of the excited state (singlet vs triplet) is dependent on aromatic substitution.