By Alan R. Katritzky (Ed.)
(from preface)Volume forty three of Advances in Heterocyclic Chemistry consists of six chapters by way of a global set of authors. David Hewitt (Australia) offers us with the 1st to be had entire assessment of heterocyclic 6-membered earrings containing phosphorus and nitrogen as heteroatoms: the azophosphorins.Chapters 2 and three, either authored by way of Wilhelm Flitsch (Federal Republic of Germany), deal, respectively, with the chemistry of the azaazulenes (not formerly lined given that 1958) and of hydrogenated porphyrins, a category of accelerating value in biochemical strategies. The reactivity of ring-nitrogen atoms in azines towards electrophiles is roofed by means of M. R. Grimmett (New Zealand) and B. R. T. Keene (England) in bankruptcy 4.The longest bankruptcy of this quantity, authored by way of Roger Gallo and Christian Roussel (France) and Ulf Berg (Sweden), offers a complete account of the quantitative therapy of steric results in hcteroaromatic compounds—a topic that has been complicated considerably via those authors. ultimately, V. N. Charushin and O. N. Chupakhin (USSR) and H. С van der Plas (The Netherlands) overview reactions of azines with bifunctional nucleophiles.
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These have been investigated for the cases where X = electron pair, 0, S, and Se. As the coordination number of the phosphorus atom increases, there is an increasing axial orientation of the phenyl on phosphorus. Configuration C is disfavored when R = benzyl and X = 0 or S. Ph X I II -- -- L y r xspqJ-R R Ph’P-N R R A B R X I II Ph’P-1 LY R C (69) There have also been some molecular orbital (MO) calculations using CND0/2, which were confirmed by NMR studies (85IZV1296). For 70, when X = S, the methyl group is equatorial and the N H bonds are axial.
N. G. Khusainova, Z. A. Bredikhina, A. D. Sinitsa, V. I. Kal’chenko, and A. N. Pudovik, Zh. Ohshch. Khim. 52(4) 789 (1982). N. K. Maidanovich, S. V. Iksanova, and Y. G. Gololobov, Zh. Obshch. Khim. 52(4), 930 (1982). N. I. Demidova, A. 1. Bokanov, 0. S. Medvedev, and B. I. Stepanov, Zh. Obshch. Khim. 52(5), 1099 (1982). 34 82ZOB2172 82ZOB2465 83AJC2095 83CJC427 831ZV418 83IZV432 831ZV1379 83PAC409 83PS73 84AJC205 84AJC1631 84A P I053 84CC200 84CZ402 84JBC 136I 84M11 84PS159 84US P4433149 85IZV1296 8SMI1 DAVID HEWITT [Refs.
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