Anion Reactions of trans-1,3-Dithiolane 1,3-Dioxide with Aldehydes and Comparison with trans-1,3-Dithiane 1,3-Dioxide

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 1139-1145

  Aggarwal, Varinder K ^a   Schade, Steffen ^a   Adams, Harry ^a  

^a UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000999902     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9619443     Document Type: Article

References (31)

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8. For reviews see: (a) Gröbel, B. T.; Seebach, D. Synthesis 1977, 357-402. (b) Page, P. C. B.; van Niet, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643-7677. (c) Hanack, M., ed. Houben-Weyl, Methoden der Organischen Chemie; Thieme: Stuttgart, 1993; Vol. E19d, pp 970-992.
9. For reviews see: (a) Gröbel, B. T.; Seebach, D. Synthesis 1977, 357-402. (b) Page, P. C. B.; van Niet, M. B.; Prodger, J. C. Tetrahedron 1989, 45, 7643-7677. (c) Hanack, M., ed. Houben-Weyl, Methoden der Organischen Chemie; Thieme: Stuttgart, 1993; Vol. E19d, pp 970-992.
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26. Due to the poor solubility of 10 in etheral solvents, a pyridine/ THF solvent system had to be used in all the reactions. Warming of 10 in this solvent mixture and subsequent cooling led to the formation of a fine suspension that was used in the following reactions. Extremely dilute reactions can be conducted in neat THF without changing the selectivity (see ref 3a).
27. We have found previously that the nature of the quench of 2 was critical (see ref 3a). Best results were obtained in a fast quench when the reaction mixture was added to a rapidly stirring solution of HCl (aq) in EtOH. We therefore used the same methodology to quench 5.
28. a measurements.
29. a of 24.9. See ref 19.
30. The author has deposited atomic coordinates for 11a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK.
31. Aggarwal, V. K.; Davies, I. W.; Franklin, R.; Maddock, J.; Mahon, M. F.; Molloy, K. C. J. Chem. Soc., Perkin Trans. 1 1994, 2363-2368.