2,3-Diazabicyclo[2.1.1]hex-2-ene. Synthesis and Thermal Decomposition

Journal of Organic Chemistry

Volumn 46, Issue 20, 1981, Pages 4092-4093

  Chang, Moon Ho ^a   Dougherty, Dennis A ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042904735     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00333a040     Document Type: Letter

References (12)

1. Engel, P. S. Chem. Rev. 1980, 80, 99-150.
2. Adam, W.; De-lucchi, O. Angew Chem., Int. Ed. Engl. 1980, 19, 762-79.
3. Mirbach, M. J.; Liu, K.-C.; Mirbach, M. F.; Cherry, W. R.; Turro, N. J.; Engel, P. S. J. Am. Chem. Soc. 1978, 100, 5122-9.
4. Roth, W. R.; Martin, M. Tetrahedron Lett. 1967, 4695-8.
5. Gassman, P. G. Acc. Chem. Res. 1971, 4,128-36.
6. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-5.
7. We have found it to be more convenient to work with 7b: *H NMR (CDCls) a 1.75 (dd, 2 H. H.), 2.30 (m, 2 H. Hb), 3.08 (s, 3 H), 4.70 (t, 2 H. H5); complete spectral simulation gives: = 6.5, = 8.4, = 2.0 Hz; lSC NMR (CDC1S) S 25.74 (CH3), 40.55 (CH2), 62.32 (CH), 161.30 (C=0); IR (CHC13) 1720 cm'1; mp 134-134.5 °C. Anal. Calcd for (C7-H,N302) C. H, N.
8. Gassman, P. G.; Mansfield, K. T. Org. Synth. 1969, 49,1-6. We have obtained better yields using cupric bromide instead of cupric chloride.
9. lH NMR (C6D6) a 1.22 (m, 2 H), 1.60 (dd, 2 H) 4.40 (t, 2 H); preliminary spectral simulation gives coupling constants essentially identical with those for 7b; 13C NMR (CC14) δ 59.01 (CH2), 76.36 (CH); mp (sealed tube) 63-4 °C; IR (CC14): 3020, 2960, 2870,1475,1430,1260, 1210,1100,1015,960 cm-1; mass spectrum (degassed sample, 15 eV), m/e 54 (98), 39 (100), 28 (55).
10. Wildi, E. A.; Van Engen, D.; Carpenter, B. K. J. Am. Chem. Soc. 1980, 102, 7994-6.
11. Kao, J.; Huang, T.-N. J. Am. Chem. Soc. 1979, 101, 5546-57.
12. Calculations performed in the present work using the force field of ref 11.