By W Parker;
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H. Goh, J. Chem. , 1973,678. T. Greibrokk, Acta Chem. , 1973,27, 3207. G. W. Gokel, J. P. Shepherd, and W. P. Weber, J. Org. , 1973,38, 1913. D. F. Hayman, Ger. Offen. 2201 514 (Chem. , 1973,78, 3793). g. the tris-adduct ( 1 99) from 1,3,5-trivinylbenzene in 75 % yield. lO' Simple alkylarylammonium salts are not necessarily the best catalysts for the phase-transfer method. It was demonstrated earlier that use of cationic micellar agents such as cetyltrimethylammonium chloride or the detergent CentrimideBcan be very effective and this has now been applied'" to the formation of bis-dihalogeno-carbene adducts of the naphthalene (203) and the benzocycloheptadienone (204).
1973, 106, 511. lo' lo' E. V. Dehmlow, H. -C. Hass, Annalen, 1973, 1063. J. Tsunetsugu, M. S. Chem. , 1973, 363. Alicyclic Chemistry 38 OMe OMe @ Me MeO& Me0 \ / OMe OMe It was initially reported that generation of dibromocarbene by the phasetransfer-catalysed method gave poor results. 'O3 were able to obtain reasonable yields (40-72 %) by employing longer reaction times (1-4 days), 1,2-divinylbenzene,for example, giving the adduct (205) in 50% yield. However, the di-adduct of tetramethylallene with dibromocarbene was obtained in only 10 % yield, compared with a 90% yield of the bis-dichlorocarbene adduct'" by the same method.
This proved not to be a very general route, crotonate furnishing only 30% of the cyclopropane (265; R = Me) and the reaction with cinnamate failing completely. 141 140 141 Y. Kawakami and T. Tsuruta, Bull. Chem. Japan, 1973,46,2262. F. Gaudemare-Bardone and M. Gaudemar, Bull. chim. France, 1973,3467. Alicyclic Chemistry 52 IM C0,Et C0,Et / C0,Et C0,Et C0,Et (263) (259)+ RCHO - a; X b:X Br = H = - Br I C0,Et RCH-Cl I (362) C0,Et OMgBr (266) K ' = Me, Pr, or Ph Sodium hydride will effect hydrogen chloride elimination from the activated ally1 chlorides (267) and addition in toluene to electrophilic olefins (268) furnishes the vinylcyclopropanes (269a)and (269b)with the former predominating over the latter.
Alicyclic Chemistry Vol. 3 by W Parker;