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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. g. g. l13Dimedone is also a suitable precursor, but the sequence fails with acyclic 1,3-diones. g. g. 'l4 (85) (86) X = C1, Br, or I Reagents: i, MeS02CI-K2C0,; ii, PhCH2NEt3X-BF, n ?
Russell, J. Cliem. , Chem. , 1981, 434. Saturated and Unsaturated Hydrocarbons 35 Ketones can also be converted into their a-isopropenyl derivatives using the hyl isopropen yl ether)]'[BFJ. 56 complex [C5H5Fe(CO)2(et Dianions of 2-alkenyloxyacetic acids (125) undergo smooth Wittig rearrangement at -78°C to give, following oxidative decarboxylation, good yields of P,y- unsaturated aldehydes. '59Vinyl or allyl reagents give 3,6- or 3,7-dienoic acids, respectively. l6l By contrast, the alkoxides resulting from hydride or alkyl-lithium addition to 2-vinylcyclobutanones undergo rearrangement at 25-70 "C to give 156 15' 31'' 159 T.
Sano, S. Aoki, and M. , 1981, 22,2675. -D. Choi, H. Maeda, and H. , 1981,22, 1343; K. Tanaka, M. Terauchi. and A. Kaji, Chem. , 1981,315. T. Nakai, K. Tanaka, K. Ogasawara, and N. Ishikawa, Chem. , 1981. 1289. T. Nakai, H. Setoi, and Y . Kageyama. , 1981, 22,4097. Saturated and Unsaturated Hydrocarbons 41 In an alternative method, cyclopropanecarboxylates of the type (140), prepared from benzyl sulphones and ethyl 4-bromocrotonate, are converted into EYE-5 aryl-2,4-dienoates (141) on treatment with potassium t - b ~ t o x i d e .
A review of the literature published during 1981 by Frank Northen Magill
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