Halton, Brian; Boese, Roland; Dixon, Gareth M.:

Studies in the cycloproparene series: Unexpected products from Peterson olefinations.

In: European Journal of Organic Chemistry, (2003) ; Nr. 23, S. 4507-4512
ISSN: 1434-193X
Zeitschriftenaufsatz / Fach: Chemie
Abstract:
Reaction of tetraphenylcyclopentadienone with (1H-cyclopropa[b]naphthalen-1-yltrimethyl)silane anion [derived by monodesilylation of 1,1-bis(trimethylsilyl)cyclopropa[b]naphthalene] gives the 1-(5'-cyclopentadienyl)substituted cycloproparene from simple anion addn. to the carbonyl group rather than fulvalene from loss of Me3SiO-. Reactions of (1H-cyclopropa[b]naphthalen-1-yltrimethyl)silane anion with p-(trifluoromethyl)benzaldehyde and thiophene-2-carboxaldehyde give the expected exocyclic olefins, 1-[[3-(trifluoromethyl)phenyl]methylene]-1H-cyclopropa[b]naphthalene and 2-(1H-cyclopropa[b]naphthalen-1-ylidenemethyl)thiophene. In contrast, 3,6-dimethoxy-1H-cyclopropa[b]naphthalen-1-yltrimethylsilane anion, obtained from a cycloproparene deriv., gives a C1 unsubstituted cycloproparene and Tishchenko products, p-(trifluoromethyl)benzyl p-(trifluoromethyl)benzoate and 2-thienylmethyl 2-thiophenecarboxylic acid 2-thienylmethyl ester.

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