Solubilization of the primary nitrene sources (tosyliminoiodo)arenes (ArINTs)

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 191-194

  Macikenas, Dainius ^a   Meprathu, Bindu V ^a   Protasiewicz, John D ^a  

^a CASE WESTERN RESERVE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TERTIARY AMINE;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLID STATE; SOLUBILIZATION;

EID: 0032518773     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10522-6     Document Type: Article

References (25)

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7. 3): δ 2.30 (s, 3H), 3.18 (s, 17H), 7.00 (d, J = 7.6 Hz, 2H), 7.21-7.14 (m, 2H), 7.42-7.32 (m, 1H), 7.56 (d, J = 7.8 Hz, 2H), 7.75 (d, J = 8.2 Hz, 2H).
8. (8) SPARTAN, Version 4.1, Wavefunction, Inc., Irvine, CA, 1996.
9. (9) The coordinates of the I, N, O, and S atoms were frozen in positions obtained from X-ray structural data for PhINTs.
10. 2 (CNDO/2 and extended Hückel) see: Mylonas, V. E.; Sigalas, M. P.; Katsoulos, G. A.; Tsipis, C. A.; Varvoglis, A. G. J. Chem. Soc. Perkin Trans. 2 1994, 1691-1696.
11. ICl-ave = 2.45(1)Å; Cl-I-Cl = 179.1° in Archer, E. M.; van Schalkwyk, T. G. D. Acta Cryst. 1953, 6, 88-92;
12. ICl = 2.457(2), 2.530(1)Å; Cl-I-Cl = 176.8(1)° in reference 2;
13. ICl = 2.491(4), 2.469(4)Å; Cl-I-Cl = 178.4(1)° in Protasiewicz, J. D. J. Chem. Soc. Chem. Comm. 1995, 1115-1116.
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20. (18) A 20% yield of aziridine is obtained in the absence of N-oxides. For a related aziridination of styrene with PhINTs catalyzed by Mn(salen)Cl (salen = N,N′-bis(salicyldine)-1,2-ethylenediamine) see O'Connor, K. J.; Wey, S.-J.; Burrows, C. J. Tetrahedron Lett. 1992, 33, 1001-1004.
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