Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry - download pdf or read online

ISBN-10: 085186502X

ISBN-13: 9780851865027

ISBN-10: 1847555500

ISBN-13: 9781847555502

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J. Parry, R. F. Myers, T. A. Bryson, and D. H. Miles, J . Amer. Chem. ,1971,93, 4332; W. S. Johnson, M. B. Gravestock, and B. E. , p. 4334. R. S. Macomber, Tetrahedron Letters, 1970,4639. Acetylenes, Allenes, and Olefins 25 @' Me (93) J 0H (95) RadicaZ Addition. '~ The high yields of crystalline products (102) obtained imply that in the mechanism (Scheme 7), chain transfer by the sulphonyl iodide (k3)is much faster than isomerization of the intermediate vinyl radical (k2). The trans-addition was confirmed by zinc-acetic acid reduction to the sulphone, and by X-ray analysis of one of the adducts.

Chem. ,1971,93, 4332; W. S. Johnson, M. B. Gravestock, and B. E. , p. 4334. R. S. Macomber, Tetrahedron Letters, 1970,4639. Acetylenes, Allenes, and Olefins 25 @' Me (93) J 0H (95) RadicaZ Addition. '~ The high yields of crystalline products (102) obtained imply that in the mechanism (Scheme 7), chain transfer by the sulphonyl iodide (k3)is much faster than isomerization of the intermediate vinyl radical (k2). The trans-addition was confirmed by zinc-acetic acid reduction to the sulphone, and by X-ray analysis of one of the adducts.

D. Landor, and S. R. Landor, J . Chem. (C), 1971, 667; see also J. -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.

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Aliphatic, Alicyclic and Saturated Heterocyclic Chemistry Volume 1 Part 1 a review of the literature published during 1970 and 1971


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