Ring-expansion of an aziridinone to a hexahydrotriazine through the agency of a novel rearrangement

Tetrahedron Letters

Volumn 37, Issue 48, 1996, Pages 8695-8698

  Yusoff, Mashitah M ^a   Talaty, Erach R ^a  

^a WICHITA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; THIOSEMICARBAZIDE; TRIAZINE DERIVATIVE;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 0030602198     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02039-4     Document Type: Article

References (10)

1. 1. Lengyel, I.; Sheehan, J.C. Angew. Chem. Int. Ed. Engl. 1968, 25.
2. 2. L'abbe, G. Angew. Chem. Int. Ed. Engl. 1980, 276.
3. 3. Talaty, E.R.; Dupuy, A.E., Jr.; Utermohlen, C.M. J. Chem. Soc., Chem. Commun. 1971, 16.
4. 4. Matsumoto, K.; Rapoport, H. J. Org. Chem. 1968, 33, 552; Barker, P.L.; Gendler, P.L.; Rapoport, H. J. Org. Chem. 1981, 46, 2455.
5. 4. Matsumoto, K.; Rapoport, H. J. Org. Chem. 1968, 33, 552; Barker, P.L.; Gendler, P.L.; Rapoport, H. J. Org. Chem. 1981, 46, 2455.
6. 5. Kenyon, G.L.; Rowley, G.L. J. Am. Chem. Soc. 1971, 93, 5552.
7. 6 The close proximity of the signals for the two tert-butyl groups appears to be a convenient way of determining that the open-chain product from 1(a) and simple nucleophiles is derived from acyl-nitrogen cleavage. The difference in these two signals for the corresponding product from 1(a) and methanol is δ 0.11 ppm.
8. 7. Hill, J.H.M. J. Org. Chem. 1965, 30, 620.
9. 8. Brace, N.O. J. Org. Chem. 1993, 58, 1804 (Scheme IV in this paper).
10. ∥O-N-Ph via 1,3-diphenylaziridinone. However, the involvement of this aziridinone, which has never been isolated or even detected, is not obligatory: dimerization of the amide anion could account for the piperazinedione.