Moderate generation of sulfenylnitrenes from novel N-sulfenylsulfodiimides

Tetrahedron Letters

Volumn 48, Issue 3, 2007, Pages 427-430

  Yoshimura, Toshiaki ^a   Fujie, Tetsuo ^a   Fujii, Takayoshi ^b  

^a UNIVERSITY OF TOYAMA   (Japan)

^b NIHON UNIVERSITY   (Japan)

Author keywords

4 Sulfanenitrile; DFT calculation; N Sulfenylsulfodiimide; Sulfenylnitrene

Indexed keywords

1 PHENYLPROPENE; 2,4 DINITROPHENYLSULFENYLNITRENE; ALKENE; AZIRIDINE DERIVATIVE; IMIDE; N SULFENYLAZIRIDINE; N SULFENYLIMINOSULFONIUM SALT; N SULFENYLSULFODIIMIDE; N SULFENYLSULFOXIMIDE; NITROGEN DERIVATIVE; S,S DIPHENYL N (2 NITROPHENYLSULFENYL)SULFODIIMIDE; S,S DIPHENYL N (2,4 DINITROPHENYLSULFENYL)SULFODIIMIDE; S,S DIPHENYL N TOSYLSULFIMIDE; S,S DIPHENYL N TOSYLSULFODIIMIDE; SULFENYL CHLORIDE; SULFENYLNITRENE; SULFUR DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CIS ISOMER; HEAT TREATMENT; HIGH TEMPERATURE; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; TRANS ISOMER;

EID: 33845399895     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.11.078     Document Type: Article

References (15)

1. Yoshimura T., Hamada K., Imado M., Hamata K., Tomoda K., Fujii T., Morita H., Shimasaki C., Ono S., Tsukurimichi E., Furukawa N., and Kimura T. J. Org. Chem. 62 (1997) 3802
2. Yoshimura T. Rev. Heteroat. Chem. 22 (2000) 101
3. Fujii T., Kousaka T., and Yoshimura T. Tetrahedron Lett. 43 (2002) 5841
4. Atkinson R.S., and Judkins B.D. J. Chem. Soc., Perkin Trans. 1 (1981) 2615
5. Atkinson R.S., Judkins B.D., and Khan N. J. Chem. Soc., Perkin Trans. 1 (1982) 2491
6. Atkinson R.S., Lee M., and Malpass J.R. J. Chem. Soc., Chem. Commun. (1984) 919
7. Atkinson R.S., and Awad S.B. J. Chem. Soc., Perkin Trans. 1 (1977) 346
8. Michida T., and Sayo H. Chem. Pharm. Bull. 42 (1994) 27
9. Kaszynski P., and Young Jr. V.G. J. Am. Chem. Soc. 122 (2000) 2087
10. Oae S., Akutagawa K., and Furukawa N. Phosphorous sulfur 19 (1984) 223
11. Appel R., and Vollmer G. Chem Ber. 103 (1970) 2555
12. -1 (S{double bond, long}N).
13. The sulfenylating reagents, 2,4-dinitro- and 2-nitrobenzenesulfenyl chlorides, used are relatively stable and commercially available.
14. N-Sulfenylated sulfodiimide was unable to see the parent peek by EI and FAB mass spectrum.
15. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery Jr. J.A., Vreven T., Kudin K.N., Burant J.C., Millam J.M., Iyengar S.S., Tomasi J., Barone V., Mennucci B., Cossi M., Scalmani G., Rega N., Petersson G.A., Nakatsuji H., Hada M., Ehara M., Toyota K., Fukuda R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Klene M., Li X., Knox J.E., Hratchian H.P., Cross J.B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R.E., Yazyev O., Austin A.J., Cammi R., Pomelli C., Ochterski J.W., Ayala P.Y., Morokuma K., Voth G.A., Salvador P., Dannenberg J.J., Zakrzewski V.G., Dapprich S., Daniels A.D., Strain M.C., Farkas O., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Ortiz J.V., Cui Q., Baboul A.G., Clifford S., Cioslowski J., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Gonzalez C., and Pople J.A. Gaussian 03, Revision D.01 (2004), Gaussian, Inc., Wallingford, CT