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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.