A NEW AND EFFECTIVE METHOD FOR THE LOW-TEMPERATURE GENERATION OF SULFONIUM YLIDES FROM ALLYL SULFIDES

被引：14

作者：

HARTLEY, RC

WARREN, S

RICHARDS, IC

机构：

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

[2] SCHERING AGROCHEM LTD,SAFFRON WALDEN CB10 1XL,ESSEX,ENGLAND

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1994年 / 05期

关键词：

D O I：

10.1039/p19940000507

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allyl 4-methoxyphenyl sulfides can be converted into sulphonium ylides which undergo [2,3] sigmatropic rearrangement in high yield and with excellent stereoselectivity by repeated alternate additions of a diazonium salt and tetrafluoroboric acid at low temperature. Under these conditions, side reactions are suppressed and both cyclic and open-chain compounds, including one containing a tertiary amine, give homoallylic sulfides in good yield. Epoxides may be made from the products.

引用

页码：507 / 513

页数：7

共 33 条

[1] PHENYLTHIO(PHS) MIGRATION IN THE STEREOCONTROLLED SYNTHESIS OF ALLYLIC ALCOHOLS WITH 1,4 RELATED CHIRAL CENTERS
AGGARWAL, VK
WARREN, S
[J]. TETRAHEDRON LETTERS, 1986, 27 (01) : 101 - 104
[2] SYNTHESIS OF COMPOUNDS WITH 1,4-RELATED CHIRAL CENTERS BY PHENYLTHIO MIGRATION - SYN AND ANTI-E-2,4-DIMETHYLHEX-3-ENE-1,5-DIOL
AGGARWAL, VK
WARREN, S
[J]. TETRAHEDRON LETTERS, 1987, 28 (17) : 1925 - 1928
[3] TRANSFORMATION OF CYCLIC ALPHA-PHENYLTHIO ALDEHYDES BY STEREOSELECTIVE ALDOL REACTIONS AND PHENYLTHIO MIGRATION INTO SPIROCYCLIC LACTONES AND ETHERS, AND E-ALLYLIC ALCOHOLS WITH 1,4-RELATED CHIRAL CENTERS
AGGARWAL, VK
COLDHAM, I
MCINTYRE, S
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (02): : 451 - 460
[4] YLIDE FORMATION AND REARRANGEMENT IN REACTION OF CARBENE WITH DIVALENT SULFUR-COMPOUNDS
ANDO, W
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1977, 10 (05) : 179 - 185
[5] ANDO W, 1978, CHEM DIAZONIUM DIAZO, P445
[6] SELECTIVE TRANSFORMATION OF 2,3-EPOXY ALCOHOLS AND RELATED DERIVATIVES - STRATEGIES FOR NUCLEOPHILIC-ATTACK AT CARBON-1
BEHRENS, CH
KO, SY
SHARPLESS, KB
WALKER, FJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (26) : 5687 - 5696
[7] BLACKBURN GM, 1968, J CHEM SOC CHEM COMM, P1261
[8] STEREOCONTROLLED AMIDOCYCLIZATIONS WITH PHENYLTHIO MIGRATION
COLDHAM, I
WARREN, S
[J]. TETRAHEDRON LETTERS, 1989, 30 (43) : 5937 - 5940
[9] STEREOSPECIFIC PHENYLTHIO MIGRATIONS IN THE SYNTHESIS OF SPIROCYCLIC LACTONES AND ETHERS FROM N-METHYL-4-PIPERIDONE AND QUINUCLIDIN-3-ONE
COLDHAM, I
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (18): : 2303 - 2307
[10] SYNTHESIS OF CYCLIC AMINES AND ALLYLIC SULFIDES BY PHENYLTHIO MIGRATION OF BETA-HYDROXY SULFIDES
COLDHAM, I
WARREN, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14): : 1637 - 1656

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