REARRANGEMENTS OF PHENYLTHIO SUBSTITUTED 1,N-DIOLS WITH TOLUENE-P-SULFONIC ACID AND WITH TOLUENE-P-SULFONYL CHLORIDE

被引：28

作者：

DJAKOVITCH, L

EAMES, J

JONES, RVH

MCINTYRE, S

WARREN, S

机构：

[1] UNIV CAMBRIDGE,CHEM LAB,CAMBRIDGE CB2 1EW,ENGLAND

[2] ZENECA FINE CHEM MFG ORG,GRANGEMOUTH FK3 8XG,SCOTLAND

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 10期

关键词：

D O I：

10.1016/0040-4039(95)00055-H

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rearrangement of a series of 1,n diols (n=2 to 12), one OH group having an adjacent PhS group, under the two sets of conditions in the title, gives single compounds in high yield drawn from four possible classes of product The effects of chain length help in our understanding of the mechanism of the rearrangements.

引用

页码：1723 / 1726

页数：4

共 11 条

[1] Aggarwal, Coldham, McIntyre, Warren, Transformation of cyclic ?-phenylthio aldehydes by stereoselective aldol reactions and phenylthio migration into spirocyclic lactones and ethers, and E-allylic alcohols with 1,4-related chiral centres, Journal of the Chemical Society, Perkin Transactions 1, pp. 451-460, (1991)
[2] Chibale, Hartley, Jenkins, Simons, Warren, Tetrahedron Lett., 34, pp. 6783-6786, (1993)
[3] Coldham, Warren, Synthesis of cyclic amines and allylic sulfides by phenylthio migration of ?-hydroxy sulfides, Journal of the Chemical Society, Perkin Transactions 1, pp. 1637-1656, (1993)
[4] McIntyre, Warren, Tetrahedron Lett., 31, pp. 3457-3460, (1990)
[5] McIntyre, Sansbury, Warren, Tetrahedron Lett., 32, pp. 5409-5412, (1991)
[6] Sansbury, Warren, Tetrahedron Lett., 33, pp. 539-542, (1992)
[7] Sansbury, Warren, Tetrahedron Lett., 32, pp. 3425-3428, (1991)
[8] VanNieuwenhze, Sharpless, J. Am. Chem.. Soc, 115, pp. 7864-7865, (1993)
[9] Villa, Warren, [1,4] Phenylthio migrations in the rearrangement of 2,4,4-tris(phenylthio)butanols, Journal of the Chemical Society, Perkin Transactions 1, pp. 2953-2966, (1994)
[10] Eaton, Cooper, Johnson, Mueller, J. Org. Chem., 37, pp. 1947-1950, (1972)

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