Regio- and stereoselective deuteration of allylic chlorides controlled by neighboring alcohol or ether groups

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4154-4156

  Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040551988     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960188y     Document Type: Article

References (11)

1. For a review, see: Magid, R. M. Tetrahedron 1980, 36, 1901.
2. Andersson, P. G.; Schab, S. Organometallics 1995, 14, 1.
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4. N2′ syn displacements of allylic acetates in the analogous formation of vinylcyclopropanes has previ-ously been reported: Bäckvall, J. E.; Vågberg, J. O.; Genét, J. P. J. Chem. Soc., Chem. Commun. 1987, 159.
5. Gorzynski Smith, J. Synthesis 1984, 629.
6. 6b In this case nearly identical reactivities were observed for both cis- and trans-4-(phenylthio)-2-cyclohexen-1-yl 3,5-dinitrobenzoate, and this was explained by a common intermediate episulfonium ion.
7. (b) Uebel, J. J.; Milaszewski, R. F.; Arlt, R. E. J. Org. Chem. 1977, 42, 585.
8. The 3,4-epoxycyclohexene was prepared from 1,3-cyclohexadiene according to the method reported by Korach, M.; Nielsen, D. R.; Rideout, W. H. J. Am. Chem. Soc. 1960, 82, 4328.
9. (a) Bäckvall, J. E.; Nyström, J. E.; Nordberg, R. E. J. Am. Chem. Soc. 1985, 107, 3676.
10. (b) Bäckvall, J. E.; Granberg, K. L.; Hopkins, R. B. Acta Chem. Scand. 1990, 44, 492.
11. Schink, H. E.; Petterson, H.; Bäckvall, J. E. J. Org. Chem. 1991, 56, 2769.