An unprecedented Favorski-like ring contraction of the 1,3,4- oxadiazinone ring to a bimane

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5039-5040

  Allen, Aberdeen ^a   Anselme, J P ^a  

^a UNIVERSITY OF MASSACHUSETTS BOSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZINONE; 3,4,6,7 TETRAPHENYL 1,5 DIAZABICYCLO[3.3.0]OCTA 3,6 DIENE 2,8 DIONE; 3,6 DIHYDRO 5,6 DIPHENYL 3 [CARBO TERT BUTOXY] 1,3,4 OXADIAZIN 2 ONE; DIAZACYCLOPENTADIENONE; UNCLASSIFIED DRUG;

ARTICLE; COMBUSTION; CRYSTAL STRUCTURE; DATA ANALYSIS; DRUG SYNTHESIS; MASS SPECTROMETRY; X RAY CRYSTALLOGRAPHY;

EID: 0030586207     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01011-8     Document Type: Article

References (10)

1. 1. Allen, A.; Anselme, J.-P., Bull. Soc. Chim. Belges 1995, 104, 577-578.
2. 2. Rosenblum, M.; Fuchs, B., J. Am. Chem. Soc., 1968, 90, 1061-1062 and earlier papers.
3. 4: C, 68.17; H, 5.72; N, 7.95. Found: C, 68.15; H, 5.76; N, 7.83.
4. 6: C, 66.36; H, 6.24; N, 6.19. Found: C, 66.45; H, 6.29; N, 6.06.
5. 5. Kosower, E. M. et al., J. Am Chem. Soc. 1978, 100, 6516-6518; 1980, 102, 4983-4993. See also Rees and Yelland [J. Chem. Soc. Perkin 1 1973, 221-225 for the isolation of the anti isomer of 3.
6. 5. Kosower, E. M. et al., J. Am Chem. Soc. 1978, 100, 6516-6518; 1980, 102, 4983-4993. See also Rees and Yelland [J. Chem. Soc. Perkin 1 1973, 221-225 for the isolation of the anti isomer of 3.
7. 5. Kosower, E. M. et al., J. Am Chem. Soc. 1978, 100, 6516-6518; 1980, 102, 4983-4993. See also Rees and Yelland [J. Chem. Soc. Perkin 1 1973, 221-225 for the isolation of the anti isomer of 3.
8. 6. We are grateful to Prof. Kosower for providing a sample of 3.
9. 7. We thank Dr. Byron H. Arison (Merck & Co, Rahway, NJ) for his help in obtaining this datum.
10. 8. A referee has suggested that the ring contraction could also proceed via a 1,2-Wittig rearrangement. (equation presented)