Tricyclic Trisaminomethanes

Journal of the American Chemical Society

Volumn 102, Issue 20, 1980, Pages 6364-6365

  Atkins, Thomas J ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383618     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00540a044     Document Type: Letter

References (13)

1. J. E. Richman and T, J. Atkins, J. Am. Chem. Soc., 96, 2268 (1974); T. J. Atkins, J. E. Richman, and W. F. Oettle, Org. Synth., 58, 86 (1978).
2. J. E. Richman and H. E. Simmons, Tetrahedron, 30, 1769 (1974)
3. J. E. Richman, Tetrahedron Lett., 559 (1977)
4. T. J. Atkins, Tetrahedron Lett., 4331 (1978)
5. T. J. Atkins and J. E. Richman, Tetrahedron Lett., 4333 (1978)
6. Tetrahedron Lett., 5149 (1978).
7. U. S. Patents 4 085 106 and 4130715.
8. Elemental analyses within O.4% of theory were obtained on all new compounds.
9. The methine hydrogen of tris(dimethylamino)methane absorbs at δ 3.02 in C6D6; see: H. Weingarten and W. A. White, J. Am. Chem. Soc., 88, 850 (1966).
10. For an empirical correlation of the 1H NMR shift with amine and ether conformations, see: C. C. Price, Tetrahedron Lett., 4527 (1971).
11. F. Bohlmann, Angew Chem., 69, 641 (1957)
12. T. A. Crabb, R. F. Newton, and D. Jackson, Chem. Rev., 71, 109 (1971).
13. Calculations indicate this conformation to be ca. 6 kcal/mol more stable than the corresponding cis,cis,trans three-chair conformation: D. A. Pensak, private communication.