Diinsertion of fluorenylidene into a Sulfur-Sulfur bond of diaryl disulfides

Tetrahedron Letters

Volumn 38, Issue 52, 1997, Pages 8989-8992

  Kawamura, Yasuhiko ^a   Akitomo, Kohji ^a   Oe, Masaaki ^a   Horie, Tokunaru ^a   Tsukayama, Masao ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; DISULFIDE; FLUORENE; SULFIDE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG SYNTHESIS; IRRADIATION; REACTION ANALYSIS;

EID: 0030811447     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10402-6     Document Type: Article

References (24)

1. Ando, W. Acc. Chem. Res. 1977, 10, 179-185.
2. Ghosh, T. Sulfur Reports 1992, 12, 339-357.
3. (a) Petragnani, N.; Schill, G. Chem. Ber. 1970, 103, 2271-2273.
4. (b) Tamagaki, S.; Oae, S. Bull. Chem. Soc. Jpn. 1972, 45, 960-961.
5. (c) Field, L.; Banks, C. H. J. Org. Chem. 1975, 40, 2774-2779.
6. Ando, W.; Kumamoto, Y.; Takata, T. Tetrahedron Lett. 1985, 26, 5187-5190.
7. Alberti, A.; Griller, D.; Nazran, A. S.; Pedulli, G. F. J. Am. Chem. Soc. 1986, 108, 3024-3028.
8. Diazofluorene 1 only absorbs the incident light under the conditions.
9. (a) Evans, D. A.; Grimm, K. G.; Truesdale, L. K. J. Am. Chem. Soc. 1975, 97, 3229-3230.
10. (b) Kuwajima, I.; Abe, T. Bull. Chem. Soc. Jpn. 1978, 51, 2183-2184.
11. 2: C,78.98; H 5.40%, found: C, 78.84; H, 5.44%.
12. w = 0.041, 3360 reflections were collected.
13. 2: C, 83.58; H, 5.26%, found: C, 83.57; H, 5.50%.
14. 6, the signal broadenings were observed at room temperature possibly due to a hindered rotation around the central C-C bond, suggesting that the interaction between S-S atoms are the one in both solid and liquid states.
15. Semiempirical PM3 SCF-MO calculations were carried out with the CAChe-MOPAC software (ver. 6.1, Sony-Tektronix, Co.): Stewart, J. J. P. J. Comput. Chem. 1989, 10, 221-264.
16. 2: C, 79.18; H, 4.98%, found: C, 79.16; H, 5.16%.
17. 3) of the reaction mixture were as follows: 3a (ca. 3%), 4a (11%), and 3b (6%), 4b (trace). The majority was recovered starting materials and others were bifuorenylidene and fluorenone azine.
18. -3 M, each) for 1 week afforded 3a in 46% yield in benzene.
19. Photo- and thermal reactions of 9-fluorenone azine with 2 were also examined but no supportive results were obtained. An arylsulfinyl radical cannot be generated under the reaction conditions.
20. In stricter sense, the mechanism of the Stevens rearrangement has been recognized as a homolytic dissociation-recombination process: Baldwin, J. E.; Erickson, W. F.; Hackler, R. E.; Scott, R. M.; J. Chem. Soc., Chem. Commun. 1970, 576-578.
21. Trost, B. M.; Melvin, Jr., L. S. Sulfur Ylides; Academic Press: New York, 1975; pp. 108-127.
22. (b) Morris, D. G. Surv. Prog. Chem. 1983, 10, 218-222. Stepwise addition of fluorenylidene to 2 is possible in Path C.
23. The disulfide linkage of diaryl disulfides exists in a rigid non-planar conformation with a dihedral angle of ca. 90° between the Ar-S-S planes: Pappalardo, G. C.; Ronsisvalle, G. Tetrahedron 1972, 28, 4147-4154.
24. The corresponding photodecompositions of naphtho[1,8-ef][1,4]dithiepins have been reported: Fujii, T.; Takahashi, O.; Furukawa, N. J. Org. Chem. 1996, 61, 6233-6239.