Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry

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L. Roumestant, Tetrahedron Letters, 1971, 1027. G. Kobrich and E. Wagner, Angew. Chem. Internat. , 1970,9, 524. J. K . Crandall and G. L. Tindell, Chem. , 1970, 1411. Acetylenes, Allenes, and Olefins R2 I RL-C~C--C-OH 39 + R4CH2C(OEt)3 Hf I I ,R'CeC-CR2R3 R3 I ' 0 / R4CH2-C(OEt), \ C=C===CR2R3 / R'CH \ CO2Et 35-60 % (178) 0 " F A ArS 130 O C , I ArS02C=C=CHR2 allenyl sulphones (1 SO) involves a similar cyclic rearrangement. When optically active acetylene is used, the absolute configuration of the product, deduced from the polarizability sequence of substituents on the allene, is in agreement with a cyclic mechanism.

Smith and C. J. M. Stirling, J . Chem. ( C ) , 1971, 1530. -P. Dulcere, M. Santelli, and M. Bertrand, Cornpt. , 1970, 271, C, 585. G . Zweifel, A. Horng, and J. T. Snow, J . Amer. Chem. ,1970, 92, 1427. A. C. Cope, W. R. Moore, R. D. Bach, and H. J. S . Winkler, J . Amer. Chem. , 1970,92, 1243. Aliphatic, Alicyclic, and Saturated Heterocyclic Chemistry 40 R2 I R’--G-C=C 0 II R1 R2 R3 / HC=CLi-NH3 I 1 HeC-C-C=C ‘R4 OH I / R3 ‘R4 I R’ Re I 1 HC=C-C=C-CR3R I * CI [(f)-CBH14(PtC12)Am*] Am* = optically active a-methylbenzylamine or p-nitro-a-methylbenzylamine.

Dai, J. Amer. Chem. ,1970, 92, 1774. J. J. Gajewski and W. A. Black, Tetrahedron Letters, 1970, 899. S . R. Byrn, E. Maverick, 0. J. Muscio, K. N. Trueblood, and T. L. Jacobs, J. Amer. Cliem. ,1971, 93, 6680. T. L. Jacobs and 0. J. Muscio, Tetrahedron Letters, 1970, 4829. W. R. Moore, R. D. Bach, and T. M. Ozretich, J. Amer. Chem. ,1969, 91, 5918. D. R. Taylor, M. R. Warburton, and D. B. Wright, J. Chem. Sac. (C), 1971, 385; D. R. Taylor and D. B. , p. 391. P. D. Bartlett, Quart. , 1970, 24, 473.

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