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16' The catalysed reaction does not proceed well with the anions from 15' 160 16' R. M. Corey and D. M. T. Chan, Tetrahedron Letters, 1975,4441. R. Kopp and M. Hanack, Angew. Chem. internat. , 1975,14,821. K. Ogura, M. Yamashita, S. Furukawa, M. Suzuki, and G. Tsuchihashi, Tetrahedron Letters, 1975,2767. R. V. Stevens, P. M. Lesko, and R. Lapalme,J. Org. , 1975,40,3495: U. Schollkopf,D. Hoppe, and R. Jentsch, Chem. , 1975, 108, 1580; K. Krohn and E. , p. 3030. R. K. Sin& and S. Danishefsky, J. Org.

Ls6With the more localized anions from methyl chloroacetate and PhCC1R' + Ph &COR2 PhCH=CHCOR2 __+ (137) R' = C 0 , M e or CN; R2 = Me or Ph chloroacetonitrile the reaction is reported to take a different course, affording epoxides (see also ref. 67). ' 5 7 The tributylphosphine ligand is C0,Me MeCHClC0,Me iii I 1 + Bu'OH Me-C-CuPBu, ___+ I C1 1 ii 1 FO,Me - Bu,PCuCI I Me-C-CH,-C-Me I I c1 COzMe Me&, CN I I Cu PBu, (139) Reagents: i, Ru'OCuPBu,;ii, CH, = C(Me)CN; iii, CH, = C(Me)CN-NaH Scheme 19 essential and the route demonstrates little stereoselectivity.

Bade, Tetrahedron Letters, 1975, 3031. Yu. V. Tomilov, V. A. Smit, and 0. M. Nefedov, Izvest. Akad. Nauk. , Ser. , 1975, 2614 (Chem. , 1976,84,58 703). Yu. S. Shabarov, S. S. Mochalov, N. B. Matveeva, and I. P. Stepanova, Zhur. org. , 1975, 11, 568 (Chem. , 1975,82, 155620); Yu. S. Shabarov and S. S. , p. 1907 (Chem. S. Shabarov and L. G. , p. 1403 (Chem. , 1975,83,113 795). S. S. Dehmlow and E. V. Dehmlow, 2. , 1975,30b, 404. ~"Cleavage of (190; X = H) and (190; X = Br) is assisted (190)X = H or Br - by silver ion, but the yield of products is low ( 10%), and no meaningful conclusions can be drawn from the kinetic data Oxidative Cleavage.

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