General and Synthetic Methods Vol.6 by G Pattenden

By G Pattenden

Expert Periodical stories offer systematic and certain evaluation assurance of development within the significant components of chemical study. Written via specialists of their expert fields the sequence creates a special provider for the energetic learn chemist, providing ordinary serious in-depth bills of development particularly parts of chemistry.

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Ore. , 1981,46,3155. S . Araki, K. Minami, and Y. Butsugan, Bull. Chem. Soc. , 1981,54,629. General and Synthetic Methods 34 Novel syntheses of P,y- unsaturated ketones, free from the conjugated isomers, by acylation of (cyclopropylmethyl) trimethylsilane ( 122)ls3or l-trimethylsilyl2-methylcyclopropane (123)ls4 have been described. Acylations of the latter type are stereospecific, the trans- cyclopropane (123), for example, producing exclusively the Z-p,y- unsaturated ketone (124). 68 Addition of lithium enolates to the a-silyl aldehydes is highly erythroselective, enabling products of either E- or 2-geometry to be obtained (Scheme 58).

Bacquet, Can. J. , 1981,59,945. Y . Mori, M. Tsuboi, and M. Suzuki, Chem. Pharm. , 1981,29,2478. A. B. Smith, 111, M. A. Guaciaro, S. R. Schow, P. M. Wovkulich, B. H. Toder, and T. W. Hall, J. A m . Chem. , 1981,103,219. T. Fujisawa and K. Sakai, Chem. , 1981, 5 5 . J. C. F. , J. Org. , 1981,46,2428. A. Barco, S. Benetti, P. G. Baraldi, and D. Simoni, Synthesis, 1981, 199; N. Ono, H. Miyake, and A. Kaji, Synthesis, 1981, 1003. 25 Saturated and Unsaturated Hydrocarbons The a-(carboethoxy)vinylcuprate (84), generated by conjugate addition of lithium cyanomethylcuprate to ethyl propiolate, reacts with a,@-unsaturated acid chlorides to form divinyl ketones.

Danheiser, C. Martinez-Davila, and H. Sard, Tetrahedron, 1981,37,3943. R. L. Danheiser, C. Martinez-Davila, R. J. Auchus, and J. T. Kadonaga, J. Am. Chem. , 1981, 103,2443. F. Sato, S. Iijima, and M. , 1981,22,243. T. Imamoto, Y. Hatanaka, Y. Tawarayama, and M. , 1981,22,4987. H. Sakurai, K. Sasaki, and A. , 1981,22,745. g. Ac Pd(dba), :dppe 1:l Scheme 63 N R ~ Rlw N R ~ NHR~ 9$ 4= 1 (131) iii R' (132) L Reagents: i, CH,=CHMgBr; ii, H,O; iii, SiO, or acidic AI,O, Ally1 vinyl ether derivatives undergo smooth Claisen rearrangement at room temperature on treatment with an excess of EtzAISPh or Et,AlCl-PPh, to give high yields of y,6- unsaturated aldehydes.

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