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

Synlett

Volumn , Issue 8, 1999, Pages 1211-1214

  Eames, Jason ^a,b   Kuhnert, Nikolai ^a,c   Sansbury, Francis H ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^b QUEEN MARY UNIVERSITY OF LONDON   (United Kingdom)

^c UNIVERSITY OF SURREY   (United Kingdom)

Author keywords

Cyclisations; Heterocycles; Rearrangements; Sulfur chemistry; Thermodynamic and kinetic control

Indexed keywords

TETRAHYDROFURAN DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS; THERMODYNAMICS;

EID: 0032770015     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2814     Document Type: Article

References (15)

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2. (b) Aggarwal, V. K.; Coldham, I.; McIntyre, S.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1991, 451;
3. (c) Chibale, K.; Warren, S. J. Chem. Soc., Perkin Trans. 1 1995, 2411.
4. (a) Djakovitch, L.; Eames, J.; Jones, R. V. H.; McIntyre, S.; Warren, S. Tetrahedron Lett. 1995, 36, 1723;
5. (b) Bird, P.; Eames, J.; Jones, R. V. H.; Roddis, M.; Sturino, C. F.; O'Sullivan, S.; Warren, S.; Westwell, M. S.; Worrall, J. Tetrahedron Lett. 1995, 36, 1909;
6. (c) Sansbury F.H. and Warren S., Tetrahedron Lett. 1991, 32, 3425.
7. Eames, J.; Warren, S. Tetrahedron Lett. 1996, 37, 3525.
8. Baldwin, J. E. J. Chem. Soc. Chem. Commun, 1976, 734.
9. 2) might suggest that there is some [1,4]-OR participation but this slight difference is not conclusive. For [1,4]-OR participation see: (a) Allred, E. L.; Winstein, S. J. Am. Chem. Soc. 1967, 89, 4008;
10. (b) Martin, O. R.; Yang, F.; Xie, F. Tetrahedron Lett. 1995, 36, 47.
11. Eliel, E. L.; Pearson, W. H.; Jewell, L. M.; Abatjoglou, A. G.; Kenan, W. R. Tetrahedron Lett. 1980, 21, 331.
12. Similar sulfonium ions have been isolated some time ago: Prelog, V.; Cerkovnikov E. Justus Liebigs Ann. Chem., 1939, 537, 214.
13. (a) Eames, J.; Jones, R. V. H.; Warren, S. Tetrahedron Lett., 1996, 37, 707;
14. (b) Coldham, I.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1993, 1637.
15. 2 decomposed over 7 days to give the tetrahydropyran 4a and tetrahydrofuran 8a (67:33) as an inseparable mixture, identical spectroscopically to that obtained previously.