New PDF release: A review of the literature published during 1981

By Frank Northen Magill

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1981,22,1579. '05 a,@-Unsaturated or aromatic aldehydes give products contaminated with j3- hydroxyacetylenes. Analogous reactions with 1-trimethylsilylbut-2-yne are preferably performed at low temperatures (-60 "C) with titanium tetrachloride as catalyst. 208 X = NMe2 or OMe Y = N M e 2 , 0 M e , o r OH 1,4-Dialkoxy-2-alkynes (169) isomerize smoothly to the corresponding 1,2dienes (170) when treated with a catalytic quantity of potassium t - b u t o ~ i d e . ~ ' ~ The solvent of choice depends on whether or not the starting material has alkyl substituents.

A. Perry, Tetrahedron, 1981, 37,4027. Saturated and Unsaturated Hydrocarbons 23 (76) Reagents: i, Me,CuLi; ii, Me,SiCI; iii, PhSCH(CI1Pr"; iv, Raney Ni; v, PTAB; vi, HBr; vii, DBU Scheme 39 On heating, the p- silylsulphoxide (77) undergoes rapid syn- elimination to give the enone (78). g. AgN0, Scheme 40 '03 I. Fleming and D. A. , 1981, 22, 5095. I. Cutting and P. J. Parsons, Tetrahedron Len.. 1981, 22, 2021. 24 General and Synthetic Methods a-Phenylselenoaldehydes, which are readily converted into a,@-unsaturated aldehydes, can be formed directly under mild conditions from unactivated aldehydes using N,N- diethylbenzeneselenamide.

Kezar, 111, J. Org. , 1981, 46, 2920;D. Saindane, C. Barnurn, H. Ensley, and P. , 1981,22,3043. R. Antonioletti, M. D'Auria, G. Piancatelli, and A. , 1981,22, 1041. R. Brittelli, J. Org. , 1981,46,2514. Serota, J. R. Simon, E. B. Murray, and W. M. Org. , 1981,46,4147. -J. Brunet, C. Sidot, and P. , 1981,22,1013. 122Importantly, carbon replaces boron with retention of configuration, so the complete sequence constitutes a stereo- and regio-specific anti-Markownikoff hydrocarboxylation of acetylenes (Scheme 46).

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A review of the literature published during 1981 by Frank Northen Magill


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