Use of a chromium tricarbonyl complex in a diels–alder reaction: Improved preparation of angularly trifluoromethyl‐substituted tetrahydrophenanthrone | Zendy

BonnetDelpon Danièle | Zendy; Lequeux Thierry | Zendy; Gruselle Michel | Zendy; Malezieux Bernard | Zendy

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Use of a chromium tricarbonyl complex in a diels–alder reaction: Improved preparation of angularly trifluoromethyl‐substituted tetrahydrophenanthrone

Author(s) -

BonnetDelpon Danièle,

Lequeux Thierry,

Gruselle Michel,

Malezieux Bernard

Publication year - 1994

Publication title -

applied organometallic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.53

H-Index - 71

eISSN - 1099-0739

pISSN - 0268-2605

DOI - 10.1002/aoc.590080608

Subject(s) - chemistry , cycloaddition , chromium , diels–alder reaction , yield (engineering) , trifluoromethyl , medicinal chemistry , organic chemistry , polymer chemistry , catalysis , materials science , alkyl , metallurgy

The tricarbonyl complex prepared from 1‐trifluoromethyldihydronaphthalene and Cr(CO) 3 (NH 3 ) 3 undergoes Diels–Alder cycloaddition under high‐pressure conditions (15 kbar) to give after decomplexation by natural light and deprotection, the tetrahydrophenanthrone product in 65% yield. This new methodology allows the activation of unreactive styrenes in Diels–Alder cycloaddition.

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