Abstract
The stereospecific addition of iodine isocyanate to cyclic olefins leads via trans iodo isocyanates to trans iodo carbamates in good yields. The latter are converted by reaction with base into ethyleneimines. In this manner the following conversions were accomplished: cyclohexene to cyclohexeneimine, dihydronaphthalene to 1,2,3,4-tetrahydroanaphthalene(1,2)imine, indene to indene(1,2)imine, 2-cholestene to cholestene(2β,3β)imine, styrene to α-phenylethyleneimine. A mechanistic interpretation of the reactions involved is given.
| Original language | English |
|---|---|
| Pages (from-to) | 1037-1042 |
| Number of pages | 6 |
| Journal | Tetrahedron |
| Volume | 20 |
| Issue number | 4 |
| DOIs | |
| State | Published - 1964 |
| Externally published | Yes |
Bibliographical note
Funding Information:l a Paper III on the Chemistry of Urethanes. For paper II see ref. 7. b This investigation was supported by Public Health Service Grant CY-4474, from the National Cancer Institute. * For some examples see G. R. Pettit and J. A. Settepani, J. Org. C/rem.2 7, 2962( 1963); N. H. Cromwell and R. A. Wankel, J. Amer. Chem.S ot. 70, 1320 (1948); P. Brookes and P. D. Lawley, Biuchem. J. 80, 496 (1961); International Cancer Congress, Moscow, Angew. Chem.I ntern. Ed. 1, 600 (1962); D. V. Lefemine, M. Dann, F. Barbatschi, W. K. Hausmann, V. Zbinovsky, P. Monnikendam, J. Adam and N. Bohonos, J. Amer. Chem.S ot. 84, 3184 (1962). a o 0. E. Paris and P. E. Fanta, J. Amer. Chem.S ue. 74, 3007( 1952); b P. E. Fanta, J. Chem. Sot. 1441 (1957); 0 D. V. Kashelikar and P. E. Fanta, J. Amer. Chem.S ot. 82,4927( 1960); d P. E. Fanta, L. J. Pandya, W. R. Groskopf and H. J. Su, J. Org. C&m. 28,413 (1963). 4 F. Wintemitz, M. Mousseron and R. Dennilauler, Bull. Sot. Chim. Fr. 382( 1956). I G. Drefahl and K. Ponsold, C&m. Ber. 93,519 (1960). @A . Hassner and C. Heathcock, TetrahedronLe tters( No. 6), 393 (1963). ’ C. Heathcock and A. Hassner, Angew.C hem.7 5,344 (1963). I037
Funding
l a Paper III on the Chemistry of Urethanes. For paper II see ref. 7. b This investigation was supported by Public Health Service Grant CY-4474, from the National Cancer Institute. * For some examples see G. R. Pettit and J. A. Settepani, J. Org. C/rem.2 7, 2962( 1963); N. H. Cromwell and R. A. Wankel, J. Amer. Chem.S ot. 70, 1320 (1948); P. Brookes and P. D. Lawley, Biuchem. J. 80, 496 (1961); International Cancer Congress, Moscow, Angew. Chem.I ntern. Ed. 1, 600 (1962); D. V. Lefemine, M. Dann, F. Barbatschi, W. K. Hausmann, V. Zbinovsky, P. Monnikendam, J. Adam and N. Bohonos, J. Amer. Chem.S ot. 84, 3184 (1962). a o 0. E. Paris and P. E. Fanta, J. Amer. Chem.S ue. 74, 3007( 1952); b P. E. Fanta, J. Chem. Sot. 1441 (1957); 0 D. V. Kashelikar and P. E. Fanta, J. Amer. Chem.S ot. 82,4927( 1960); d P. E. Fanta, L. J. Pandya, W. R. Groskopf and H. J. Su, J. Org. C&m. 28,413 (1963). 4 F. Wintemitz, M. Mousseron and R. Dennilauler, Bull. Sot. Chim. Fr. 382( 1956). I G. Drefahl and K. Ponsold, C&m. Ber. 93,519 (1960). @A . Hassner and C. Heathcock, TetrahedronLe tters( No. 6), 393 (1963). ’ C. Heathcock and A. Hassner, Angew.C hem.7 5,344 (1963). I037
| Funders | Funder number |
|---|---|
| U.S. Public Health Service | CY-4474 |
| Institut National du Cancer |