Yvonne Bessiere

Synthesis of (−)-α-CIS-Bergamotene. An Efficient Prenylation Procedure

Abstract The introduction of the “isoprene unit” is an important key step in terpene synthesis and to this end, several basic routes employing organometallics have been utilised.

In the blind spot of diffusion control: 2-fluoroallyl cations and their various possibilities for stabilization

Three new model substrates of the chlorofluorocyclopropane type (I, II, and III) were submitted to silver ion-assisted ring opening. No rearrangement, but only fragmentation or direct solvolysis, occurred. In the latter case, primary rather than tertiary 2-fluoroallyl alcs. were formed almost exclusively. Nucleophilic attack at the unsubstituted terminus of the 2-fluoroallyl cation was apparently favored for steric reasons. [on SciFinder (R)]

SYNTHESES OF ORGANOFLUORINE COMPOUNDS. VIII. SOLVOLYTIC RING-OPENING OF ALKOXYCHLOROFLUOROCYCLOPROPANES- A READY ACCESS TO FLUORINATED α,β-UNSATURATED ALDEHYDES AND KETONES

1-Chloro-1-fluorocyclopropanes [I; R, R1, R2, R3 = H, OMe, Me, Me; Me, OMe, H, H; H, OMe, Me, Me2CH(CH2)3; H, OMe, Me, Me2C:CHCH2CH2; Me, Me, H, MeOCH:CMeCH2CH2; H, OEt, H, Me] were easily prepd. by cycloaddn. of ClFC: to alkenyl ethers in a 2-phase system. I were solvolyzed by heating in an aq. solvent mixt. to give 2-fluoro-2-alkenals, which were readily reduced by LiAlH4 to the corresponding 2-fluoro-2-alkenols. [on SciFinder (R)]