59901-79-0Relevant academic research and scientific papers
Elaboration of α-Substituted Benzyl Alkyl Ethers and Sulphides by Suppression of the Wittig and Related Rearrangements via Complexation to Tricarbonylchromium
Blagg, Julian,Davies, Stephen G.,Holman, Nicholas J.,Laughton, Charles A.,Mobbs, Bryan E.
, p. 1581 - 1590 (2007/10/02)
Co-ordination of benzyl alkyl ethers and sulphides to tricarbonylchromium allows α-substitution via the corresponding α-carbanions to be achieved by suppression of the Wittig and related rearrangements.Little stereoselectivity was observed in the α-methylation of tricarbonylchromium complexes of benzyl ethers derived from a variety of chiral alcohols.Excellent stereoselectivities were observed in the mono- and di-methylation reactions of tricarbonylchromium where single diastereoisomers of the α-methyl and α,α'-dimethyl complexes were formed.Deprotonation and methylation of tricarbonyl-syn-1-methoxytetralinchromium occured stereospecifically with complete retention of configuration under conditions where the corresponding anti-complex was inert.On treatment with base tricarbonyl-(3-chloropropyl benzyl ether)chromium cyclises to give tricarbonyl-(2-phenyltetrahydrofuran)chromium.Exposure of arenetricarbonylchromium complexes to air and sunlight quantitatively liberates the free arene.
