One step conversion of highly dipolarophilic olefins to α-hydroxy-β-cyanoadducts with metal fulminate

Tetrahedron Letters

Volumn 37, Issue 8, 1996, Pages 1165-1168

  You, Zhengqing ^a   Lee, Henry Joung ^a  

^a FLORIDA A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANIDE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030056342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02401-8     Document Type: Article

References (17)

1. Grundmann, C. and Grunanger, P. in The Nitrite Oxides', Springer-Verlag, New York, 1971.
2. Padwa, A (ed.), '1,3-Dipolar Cycloaddition Chemistry', Wiley-Interscience, New York, 1984.
3. Torssell, K.B.G. in 'Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis', VCH, Weinheim, 1988.
4. Carruthers, W. in 'Cycloaddition Reactions in Organic Synthesis', Pergamon, New York, 1990.
5. Among the published nitrile oxides involved in 1,3-dipolar cycloadditions, the closest to metal fulminate is probably trimethylsilanecarbonitrile oxide: (a) Brandi, A.; De Sarlo, F.; Guarna, A. and Speroni, G. Synthesis, 1982, 719.
6. (b) Kurth, M. J.; Rodriguez, M. J. and Olmstead, M. M. J. Org. Chem. 1990, 55, 283.
7. Lee, H. J. and Soliman, M. R. I. Science 1982, 215, 989.
8. Lee, H. J.; Heiman, A. S.; Taraporewala, I. B. In New Developments in Anti-Rheumatic Therapy; Rainsford, K. D. and Velo, G. P. (eds); MPT Press: Lancaster, 1989; Vol. III, 153-186.
9. Khalil, M. A.; Kwon, T.; Lee, H. J. Current Topics in Med. Chem. 1993, 1, 173.
10. You, Z.; Khalil, M. A.; Ko, D.-H. and Lee, H. J. Tetrahedron Lett. 1995, 36, 3303.
11. De Sarlo, F.; Guarna, A.; Brandi, A.; Goti, A. Tetrahedron 1985, 41, 5181.
12. Mercuric fulminate is a dangerous explosive sensitive to heat, impact and friction when dry. It should be kept away from flame, sulfuric acid or strong radiation and should be stored wet until used. See Lewis, R. J., Sr. in 'Hazardous Chemicals Desk Reference' (3rd ed.), Van Nostrand Reinhold, New York, 1993; p. 631&811.
13. Huisgen, R. and Christi, M. Chem. Ber. 1973, 106, 3291.
14. Wade, P. A. and Bereznak, J. F. J. Org. Chem. 1987, 52, 2973.
15. Kozikowski, A. P. and Adamczyk, M. J. Org. Chem. 1983, 48, 366.
16. Alkyl acrylate, styrene and norbornylene are known to be very active dipolarophiles toward benzonitrile oxide and fulminic acid (references 1 and 10) and enone 1 and 6 should also be quite active dipolarophiles due to the ring strain and activation by the carbonyl group.
17. 2). MS (PCI, 1350V): 148.1 (100, M+1).