Raphael

Raphael, Acetylenic Compounds in Organic Synthesis, 1955 (Butterworths). 

Raphael has deyised a commercial synthesis using intermediates 365A and B to provide the two halves of the molecule. B is converted in aqueous add to an isomeric alcohol. Draw this. 

Revision Problem 5 This molecule (TM 400) was used by Raphael in his synthesis of the natural product clovene. How could you make it. 

Only isomer A will be formed as the alternative cannot give a stable enolate anion (see frame 101). This is nearly the synthesis used by Raphael (Tetrahedron. 1962, 55 Proc. 

R.A. Raphael, "Acetylenic Compounds in Organic Synthesis", Butterworths Scientific Publications, London, (1955). 

Raphael, E. and de Gennes, P.G., Rubber-rubber adhesion with connector molecules. J. Phys. Chem., 96, 4002-4007 (1992). 

L ger, L., Raphael, E. and Hervet, H., Surface-anchored polymer chains their role in adhesion and friction. Adv. Polym. Sci., 138, 185-225 (1999). 

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