Studies in the Cycloproparene Series: Unexpected Products from Peterson Olefinations | Zendy

Halton Brian | Zendy; Boese Roland | Zendy; Dixon Gareth M. | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

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

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)

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research