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Download Houben-Weyl Methods in Organic Chemistry: Oraganophosphorus by Houben J., Weyl T. PDF

By Houben J., Weyl T.

Methoden der Organischen Chemie (Methods of natural Chemistry, referred to as Houben-Weyl) is a customary reference paintings for chemists engaged in natural synthesis. In volumes on compound periods, together with all Supplemental volumes, preparative equipment are taken care of comprehensively and significantly. Tables of examples examine an important equipment and express their scope. particular experimental methods are given for the easiest tools. The reactivity and extra reactions of every compound category also are awarded. The huge use of formulation schemes help in making the German-language volumes extra comfortably comprehensible to non-German readers.

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Deslongchamps P, Chenevert R, Taillefer RJ, Moreau C, Saunders JK (1975) Can J Chem 53:1601 8. Deslongchamps P, Moreau C (1971) Can J Chem 49:2465 9. Deslongchamps P, Moreau C, Fréhel D, Atlani P (1972) Can J Chem 50:3402 10. Deslongchamps P, Atlani P, Fréhel D, Malaval A, Moreau C (1974) Can J Chem 52:3651 11. Khouri F, Kaloustian MK (1978) Tetrahedron Lett 5067 12. Khouri F, Kaloustian MK (1979) J Am Chem Soc 101:2249 13. Kaloustian MK, Khouri F (1981) Tetrahedron Lett 22:413 14. Kaloustian MK, Khouri F (1980) J Am Chem Soc 102:7579 15.

O - O 1 OMe 2 3 ð67Þ H 4 229 O 230 H H+ O CO2Me O 231 H CO2Me O 232 6 Conformations of Mono and Dithioacetals 2-Alkoxytetrahydrothiopyrans were studied by Zefirov and Shekhtman [35] and the axial conformer 233 was found to predominate (90 %) over the equatorial conformer 234 when R was a methyl or a propyl group. The equilibrium of the isomeric mixture of 235 and 236 under acidic conditions was studied by Eliel and Giza [36]. The axial isomer 235 was found to constitute almost 65 % of the mixture.

In the transition state structure 36, the electron pair orbital is disposed anti to the leaving group Y and, thus, the subsequent elimination (or intramolecular SN2 reaction) is facile. In the alternate anti attack, the transition state structure resembles the twist-boat structure 38, wherein the electron pair orbital is syn to the leaving group and, thus, not facile. Thus, the difficulties in the transformation 35a ! 39b are: (a) energy-requiring twist-boat transition structure 38, (b) stereoelectronically unsupported syn elimination leading to the transformation 38 !

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