Kinetic and thermodynamic control in the synthesis of tetrahydro-pyrans and -furans from 1,4-diols by stereospecific phenylsulfanyl (PhS) migration:: Competition between exo and endo transition states and between [1,2] and [1,4] sulfanyl participation

被引：0

作者：

Eames, J ^{[1
]}

Kuhnert, N ^{[1
]}

Sansbury, FH ^{[1
]}

Warren, S ^{[1
]}

机构：

[1] Univ Cambridge, Chem Lab, Cambridge CB2 1EW, England

来源：

SYNLETT | 1999年 / 08期

关键词：

cyclisations; heterocycles; thermodynamic and kinetic control; sulfur chemistry; rearrangements;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The factors controlling the cyclisation of 1,4-diols with PhS migration to give THPs rather than THFs are reassessed. Furthermore we provide evidence for a competition between [1,2] and [1,4] sulfanyl participation and cyclisation onto a five membered cyclic sulfonium salt.

引用

页码：1211 / 1214

页数：4

共 2 条

[1] ADDITION OF LITHIATED ANIONS FROM ARYLACETONITRILES TO ALPHA,BETA-UNSATURATED ALDEHYDES - SOLVENT EFFECT ON 1,2 VERSUS 1,4 ADDITION UNDER KINETIC AND-OR THERMODYNAMIC CONTROL
WARTSKI, L
ELBOUZ, M
SEYDENPENNE, J
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1979, 177 (01) : 17 - 26
[2] Organic synthesis via transition-metal complexes, part 111 -: Spiro-fused cyclopentadienes and novel pyridinium carbonyltungstates from (1-alkynyl)carbene tungsten complexes and exo-methylene N-heterocycles.: Competition between 1,4-addition, 1,2-addition, and metathesis
Göttker-Schnetmann, I
Aumann, R
Kataeva, O
Holst, C
Fröhlich, R
ORGANOMETALLICS, 2001, 20 (13) : 2889 - 2904

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