TMM diyl-induced vinylcyclopropane fragmentation and recombination

Tetrahedron Letters

Volumn 39, Issue 14, 1998, Pages 1893-1896

  Carroll, Georgia L ^a   Little, R Daniel ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; DNA FRAGMENT;

ARTICLE; DRUG SYNTHESIS; ELECTRON TRANSPORT; GENETIC RECOMBINATION; NONHUMAN; PROTECTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0032473852     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00156-7     Document Type: Article

References (10)

1. 1. Little, R. D. Chem. Rev. 1996, 96, 93.
2. 2. Hudlicky, T.; Reed, J. W. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon: Oxford, 1991; Vol. 5, Chapter 8.1.
3. 3. a) Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
4. b) Newcomb, M. Tetrahedron 1993, 49, 1151.
5. 4. a) Gajewski, J.; Paul, G. J. Org. Chem. 1996, 61, 1399.
6. b) Gajewski, J.; Paul, G.; Kestyn, P. A.; Khorasanizadeh, S.; Lahti, P. M. J. Org. Chem. 1997, 62, 7189.
7. 5. Adam, W.; Finzel, R. J. Am. Chem. Soc. 1992, 114, 4563.
8. 6. The trans cyclopropyl diazenes have been synthesized by Mr. Peter Mikesell, UCSB.
9. 7. Moelter, K. D.; Little, R. D. Tetrahedron Lett. 1985, 26, 3417.
10. 3) δ ppm: (isomer 1): 6.22 (1H, d, J=11 Hz), 5.80 (1H, dd, J=2 Hz), 5.83 (1H, m), 5.70 (1H, br ddd), 5.52 (1H, ddd, J=11, 6, and 1.6 Hz), 3.96 (1H, br dd, J=11 Hz), 3.73 (3H, s, OMe), 3.72 (2H, m), 3.32 (1H, dd, J=11 and 6 Hz), 2.39 (1H, m), 2.22-2.10 (2H, m), 1.57 (1H, m); (isomer 2): 6.12-5.83 (3H, m), 5.36 (1H, dd, J=2 Hz), 5.32 (1H, br ddd), 3.68 (3H, s, OMe), 3.05 (1H, m), 2.97 (1H, m), 2.83 (1H, br ddd, J∼8.6 Hz), 2.72 (1H, m), 2.32 (2H, m), 2.01 (1H, m), 1.40 (1H, m).