Alicyclic Chemistry Vol. 3 by W Parker;

By W Parker;

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W. Mills, R. D. H. Murray, and R. A. S. Perkin I, 1973, 133, 42 Scheme 22 of chrysanthemic acid, which was covered in an earlier Report. In a related study, Santelli and Bertrand'" generated the carbene (219), which added to mesityl alcohol (a homologue of the reagent used by Raphael's group) to afford a single stereoisomer (220) having the threo configuration. The addition of the carbene from the same side as the OH group argues in favour of some association between the two to account for the orientation effect.

Three- and Four-mombered Rings 23 The reaction65of phenyl-lithium with cinnamyl chloride has been found to afford a complex mixture of products including diphenylcyclopropanes ( 109a) NU Scheme 9 (Scheme 10). Products (111H115) are similar to those formed from phenyllithium and 1-halogenobut-2-enes and result either by displacement reactions of phenyl-lithium on cinnamyl chloride or more probably through an intermediate carbene which cyclizes to phenylcyclopropane, this being further arylated with phenyl-lithium.

Dehmlow and E. V. Dehmlow, Annalen, 1973, 1753. M. Makosza and M. , 1973,3,305. L. Van Chau and M. Schlosser, Synthesis, 1973, 112. P. Weyerstahl, R. Mathias, and G. Blume, Tetrahedron Letters, 1973, 61 1. Three- and Four-membered Rings 39 An alternative to the two-phase system is to use higher temperatures and ethylene oxide in place of aqueous sodium hydroxide to remove the hydrogen halide generated in the reaction. This has been applied to the generation of gem-chlorofluoro- and difluoro-adducts,lo' but some of these adducts are unstable to the reaction conditions.

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