Synthesis and photopinacol rearrangement of 1a,9a‐dihydro‐1a,9b‐diphenylphenanthro[9,10‐b]oxirene

Davis Avnir; Jochanan Blum

doi:10.1002/jhet.5570170646

Synthesis and photopinacol rearrangement of 1a,9a‐dihydro‐1a,9b‐diphenylphenanthro[9,10‐b]oxirene

Davis Avnir^*
, Jochanan Blum

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Comment/debate

9 Scopus citations

Abstract

The synthesis of the title compound is described. Pinacol reduction of 2,2′‐dibenzoylbiphenyl followed by dehydration of the trans‐diol, so formed, with dimethylformamide dimethyl acetal yielded 55% of the oxirane. Irradiation of the oxide in methylene chloride at 254 nm gave 10,10‐diphenyl‐9‐(10H)phenanthrone as the major photoproduct.

Original language	English
Pages (from-to)	1349-1350
Number of pages	2
Journal	Journal of Heterocyclic Chemistry
Volume	17
Issue number	6
DOIs	https://doi.org/10.1002/jhet.5570170646
State	Published - Sep 1980

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title = "Synthesis and photopinacol rearrangement of 1a,9a‐dihydro‐1a,9b‐diphenylphenanthro[9,10‐b]oxirene",

abstract = "The synthesis of the title compound is described. Pinacol reduction of 2,2′‐dibenzoylbiphenyl followed by dehydration of the trans‐diol, so formed, with dimethylformamide dimethyl acetal yielded 55\% of the oxirane. Irradiation of the oxide in methylene chloride at 254 nm gave 10,10‐diphenyl‐9‐(10H)phenanthrone as the major photoproduct.",

author = "Davis Avnir and Jochanan Blum",

year = "1980",

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doi = "10.1002/jhet.5570170646",

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AU - Avnir, Davis

AU - Blum, Jochanan

PY - 1980/9

Y1 - 1980/9

N2 - The synthesis of the title compound is described. Pinacol reduction of 2,2′‐dibenzoylbiphenyl followed by dehydration of the trans‐diol, so formed, with dimethylformamide dimethyl acetal yielded 55% of the oxirane. Irradiation of the oxide in methylene chloride at 254 nm gave 10,10‐diphenyl‐9‐(10H)phenanthrone as the major photoproduct.

AB - The synthesis of the title compound is described. Pinacol reduction of 2,2′‐dibenzoylbiphenyl followed by dehydration of the trans‐diol, so formed, with dimethylformamide dimethyl acetal yielded 55% of the oxirane. Irradiation of the oxide in methylene chloride at 254 nm gave 10,10‐diphenyl‐9‐(10H)phenanthrone as the major photoproduct.

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AN - SCOPUS:2742583468

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IS - 6

ER -

Synthesis and photopinacol rearrangement of 1a,9a‐dihydro‐1a,9b‐diphenylphenanthro[9,10‐b]oxirene

Abstract

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