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Additional resources for Aliphatic Chemistry Volume 2
Manecke and D. Zerpner, Chem. , 1972, 105, 1943; see also S. Kobayashi, M. Shinya, T. Nakano, and H. Taniguchi, Nippon Kagakir Zasshi, 1971 92, 644 (Chem. A h . , 1972, 76, 126 6880. D. Lemarchand, N . M’Baye, and J. Braun, J. , 1972, 39, C69. W. Ried and E. Koenig, Annalen, 1972, 757, 153. 76Many acetylenes are dipolarophiles, and dimethyl acetylenedicarboxylate (DMAD), because of its ready availability, often plays this role in the formation of a variety of heterocycles. 78 Further examdes of CO,H I Ph-CHNCOPh I Me Ac,O> O-fYph -'cYph - NMe -phQph +NMC Ph Ph (loo) 74 78 77 78 Mc Me0,C' \CO,Me (99) W.
Sasaki, K. Kanematsu, and A. Kakehi, Tetrahedron Letters, 1972, 5245; J. Org. Chem. 1972,37, 3106. R. Moriarty and A. S. Chem. , 1972, 1300. la8 H. Fujita, R. Endo, K. Murayama, and T. Ichii, Bull. Chem. Japan, 1972, 45, 12' 1581, 1582. Johnson and G . S. Perkin I, 1972, 840. Johnson and G . S. Perkir' I, 1972, 844. R. A. Abramovitch, G. Grins, R. B. Rogers, J. L. Atwood, M. D. Williams, and S. Crider, J. Org. , 1972, 37, 3383. J. L. Shim, R. Niess, and A. D. Broom, J. Org. , 1972, 37, 578. P. T.
1971, 36, 3856. I** 43 the case of amines, attack on carbon predominates. Phenylbromoacetylene and diazabicyclo-octane yield (186), in a process reminiscent of the von Braun r e a ~ t i 0 n . -Several recent papers have been concerned with thermal rearrangements of acetylenes. cis-Hexa175-diyn-3-ene(187) on gas-phase pyrolysis in a flow system at 300 "C undergoes a degenerate thermal rearrangement. Thus pyrolysis of the dideuteriated analogue (188) results in scrambling of the deuterium between acetylenic and L\ (187) R (188) R = H = D R (189) R = D vinyl positions, but with either both vinyl positions or both acetylenic positions labelled only [(188) and (189)].
Aliphatic Chemistry Volume 2