By M A McKervey, Chemical Society
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Additional info for Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976
L. Chong, Austral. J . , 1976,29, 1699. H. Prinzbach, V. Wessely, and H. Fritz,Tetrahedron Letters, 1976, 2765. G. Kaup and K. RBsch, Angew. Chem. Znternat. , 1976,15, 163; K. Menke and H. , p. 165; R. Nader and A. , p. 166. Thermal equilibration of (109) leads to (110) and the stable norcaradiene (1 11) which may also be a primary product of the cyclopropanation reaction. Although the details of the monocyclopropanation product of (106; R = C0,Me) are vague (a footnote in the communication), it would appear that the electron-withdrawing methoxy-carbonyl substituents make a significant contribution to the stability of the ‘norcaradieneophane’.
Shabarov, S. G. Bandaev, E. M. Volkov, and L. D. Sychkova, Zhur. org. , 1976,12,812, 1005 (Chem. , 1976, 85, 21569, 77783); Yu. S. Shabarov, L. D. Sychkova, and S. G. , 1976, 17, 82 (Chem. , 1976,85, 5831). R. G. Salomon and R. D. Gleim, J . Org. , 1976,41, 1529. D. J. Pasto and M. F. Miles, J . Org. , 1976,41,425; D. J. Pasto, R. L. Smorada, B. L. Turini, and D. J. , p. 432. *I HgOAc HgOAc 1 (184) ii Me Me Me Me I 3 iii Reagents: i, Hg(OAc),; ii, NaBH,-AcO-; iii, H + Scheme 22 tion. ), although dependent to some extent on the nature of the electrophile, are explicable in terms of the aryl substituent best stabilizing carbonium ion character at C-3 and the alkyl substituent best stabilizing carbonium ion character at C-4.
Prendergast and W. H. Fink, J . Amer. Chem. , 1976,98,648;V. P. Zabransky and R. W. , p. 1 1 30. Three-membered Rings 23 mixture of ground and first excited states. Photolysis of cyclic aryl pinacol carbonates (70) results in cycloelimination and carbene formation. ' ' The photoinduced fragmentation of carbonyl ylides has been further studied. V. and visible irradiation of the styrene oxides (71) results in cycloelimination and carbene generation. 113u This route has provided the first report of cyanomethoxycarbonylcarbene (73; R2 = C0,Me).
Alicyclic chemistry. Vol. 6 : a review of the literature published during 1976 by M A McKervey, Chemical Society