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Photoinduced hydrogen abstraction‐coupling reaction mechanism of Δ 5 ‐steroids with substituted 1, 4‐benzoquinones via electron transfer pathways
Author(s) -
Yang ChengGen,
Jiang ZhiQin,
Zhu DunRu,
Wu ShuPing,
Yang Li,
Wu LongMin
Publication year - 2001
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20010191209
Subject(s) - chemistry , hydroquinone , photochemistry , cidnp , quinone , electron transfer , hydrogen atom abstraction , cyclic voltammetry , photoinduced electron transfer , reaction mechanism , coupling reaction , semiquinone , hydrogen , radical , stereochemistry , electrochemistry , organic chemistry , catalysis , electrode
The photochemical reaction between three A 5 ‐steroids (1–3) and a series of substituted 1,4‐benzoquinones and their mechanistic study were reported. The reaction in nitrogen atmosphere led to the formation of three products including the steroid‐quinone coupling compound (A), 7‐hydroxy derivatives of Δ 5 ‐steroids (B) and substituted 1, 4‐hydroquinone (C). Both chemical and spectrometric evidences such as UV‐Visible spectra, ESR, chemically induced dynamic nuclear polarization (CIDNP) and cyclic voltammetry (CV) verified that the title reaction underwent a predominant photoinduced electron transfer pathway via the triplet quinone.