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Studies in the Cycloproparene Series: Unexpected Products from Peterson Olefinations
Author(s) -
Halton Brian,
Boese Roland,
Dixon Gareth M.
Publication year - 2003
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300382
Subject(s) - chemistry , trifluoromethyl , benzaldehyde , thiophene , medicinal chemistry , trimethylsilyl , naphthalene , cyclopentadienyl complex , carboxylate , ion , organic chemistry , catalysis , alkyl
Abstract Reaction of tetraphenylcyclopentadienone with anion 8 derived by monodesilylation of 1,1‐bis(trimethylsilyl)cyclopropa[ b ]naphthalene ( 10 ) gives the 1‐(5′‐cyclopentadienyl)‐substituted cycloproparene 17 from simple anion addition to the carbonyl group rather than fulvalene 16 from loss of Me 3 SiO − . Reactions of anion 8 with p ‐(trifluoromethyl)benzaldehyde and thiophene‐2‐carbaldehyde give the expected exocyclic olefins 12a and 12b , respectively. In contrast, the 3,6‐dimethoxy analogue 24 , obtained from cycloproparene 20 , gives the C1 unsubstituted cycloproparene 19 and the Tishchenko products, p ‐(trifluoromethyl)benzyl p ‐(trifluoromethyl)benzoate ( 21 ) and 2‐thienylmethyl thiophene‐2‐carboxylate ( 22 ), respectively. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)