Effect of phenyl substitution on the lifetime and product distribution of cyclobutylidene: preference change in the rearrangements via 1,2-carbon shift and 1,2-hydrogen shift

Tetrahedron Letters

Volumn 47, Issue 24, 2006, Pages 3995-3999

  Takahashi, Yasutake ^a   Sakakibara, Takurou ^a   Inaba, Makoto ^a   Tomioka, Hideo ^a   Koseki, Shiro ^b   Fujimoto, Kazuyoshi ^a   Umeda, Hiroaki ^b  

^a MIE UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; CARBON; HYDROGEN;

ARTICLE; CHEMICAL STRUCTURE; LASER; MATHEMATICAL COMPUTING; PHOTOCHEMISTRY; PHOTOLYSIS; STEADY STATE; SUBSTITUTION REACTION;

EID: 33646384379     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.007     Document Type: Article

References (47)

1. Takahashi Y., Mori Y., Nakamura A., and Tomioka H. Tetrahedron Lett. 46 (2005) 8415-8418
2. Takahashi, Y. Unpublished results.
3. See also Ref. 2 for photochemistry of methylenecyclopropanes.
4. Kende A.S., Goldschmidt Z., and Smith R.F. J. Am. Chem. Soc. 92 (1970) 7606-7607
5. Gilbert J.C., and Butler J.R. J. Am. Chem. Soc. 92 (1970) 7493-7494
6. Gilbert J.C., and Luo T. J. Org. Chem. 46 (1981) 5237-5239
7. Mizuno K., Maeda H., Sugita H., Nishioka S., Hirai T., and Sugimoto A. Org. Lett. 3 (2001) 581-584
8. Mizuno K., Ichinose N., and Yoshimi Y. J. Photochem. Photobiol. A: Chem. 1 (2000) 167-193
9. In: Moss A.M., Platz M.S., and Jones Jr. M. (Eds). Reactive Intermediate Chemistry (2004), Wiley, New York
10. Majchrzak M.W., Békhazi M., Tse-Sheepy I., and Warkentin J. J. Org. Chem. 54 (1989) 1842-1845
11. Jefferson E.A., and Warkentin J. J. Am. Chem. Soc. 114 (1992) 6318-6325
12. Jefferson E.A., and Warkentin J. J. Org. Chem. 59 (1994) 455-462
13. Adam W., and Finzel R. Tetrahedron Lett. 31 (1990) 863-866
14. Warkentin J. J. Chem. Soc., Perkin Trans. 1 (2000) 2161-2169
15. Pezacki J.P., Pole D.L., Warkentin J., Chen T., Ford F., Toscano J.P., Fell J., and Platz M.S. J. Am. Chem. Soc. 119 (1997) 3191-3192
16. Pezacki J.P., Warkentin J., Wood P.D., Lustzyk J., Yuzawa T., Gudmundsdóttir A.D., and Platz M.S. J. Photochem. Photobiol. A 116 (1998) 1-7
17. Bonneau R., Hellrung B., Liu M.T.H., and Wirz J. J. Photochem. Photobiol. A 116 (1998) 9-19
18. Pezacki J.P., Wood P.D., Gadosy T.A., Lustzyk J., and Warkentin J. J. Am. Chem. Soc. 120 (1998) 8681-8691
19. Friedman L., and Schechter H. J. Am. Chem. Soc. 82 (1960) 1002-1003
20. Brinker U.H., and Schenker G. J. Chem. Soc., Chem. Commun. (1982) 679
21. Sulzbach H.M., Platz M.S., Schaefer H.F., and Hadad C.M. J. Am. Chem. Soc. 119 (1997) 5682-5689
22. Stracener L.L., Halter R.J., McMahon R.J., Castro C., and Karney W. J. Org. Chem. 65 (2000) 199-204
23. Schoeller W.W. J. Am. Chem. Soc. 101 (1979) 4811-4815
24. Wang B.-Z., and Deng C.-H. Chin. J. Chem. (1990) 102-109
25. -1).
26. Considering from the lifetime of carbene 5, it seems more likely that dimer 14 is produced by the reaction of carbene 5 with diazocyclobutane 12 rather than dimerization of carbene 5 itself. See Ref. 10 for alkene formation by the reaction of carbene with diazocompounds. Reaction of 5 with precursor 11 or involvement of the triplet state of 5 for the formation of dimer 14 is also a possibility, for which no evidence has been obtained yet.
27. Reimlinger H. Angew. Chem., Int. Ed. Engl. 1 (1962) 156
28. Reimlinger H. Chem. Ber. 97 (1964) 339-348
29. IR spectroscopic observations indicated that initially formed diazocyclobutane 12 can be photolyzed more effectively with 255 nm light.
30. Scaiano J.C. Acc. Chem. Res. 15 (1982) 252-258
31. Jackson J.E., Soundararajan N., Platz M.S., and Liu M.T.H. J. Am. Chem. Soc. 110 (1988) 5595-5596
32. Jackson J.E., and Platz M.S. In: Brinker U. (Ed). Advances in Carbene Chemistry Vol. 1 (1994), JAI Press, Stanford, CT 89
33. Platz M.S. In: Bertrand G., and FontisMedia S.A. (Eds). Carbene Chemistry (2002), Marcel Dekker, Switzerland 27
34. David A., Modarelli D.A., and Platz M.S. J. Am. Chem. Soc. 115 (1993) 10440-10441
35. Platz M.S. In: Brinker U. (Ed). Advances in Carbene Chemistry Vol. 2 (1998), JAI Press, Stanford, CT 133
36. 5
37. The assumed rate constant for pyridine ylide formation may be an upper limit because cyclobutylidenes 3 and 5 are sterically hindered by two phenyl groups.
38. *, much weaker absorption due to 12 persisted for a few seconds.
39. 20 Since rearrangements of carbenes are known to proceed through the singlet state, our calculations were limited to the singlet surfaces.
40. Schmidt M.W., Baldridge K.K., Boatz J.A., Elbert S.T., Gordon M.S., Jensen J.H., Koseki S., Matsunaga N., Nguyen K.A., Su S., Windus T.L., Dupuis M., and Montgomery Jr. J.A. J. Comput. Chem. 14 (1993) 1347-1363
41. Nakano H. J. Chem. Phys. 99 (1993) 7983-7992
42. Nakano H. Chem. Phys. Lett. 207 (1993) 372-378
43. Ditchfield R., Hehre W.J., and Pople J.A. J. Chem. Phys. 54 (1971) 724-728
44. Hehre W.J., Ditchfield R., and Pople J.A. J. Chem. Phys. 56 (1972) 2257-2261
45. Francl M.M., Pietro W.J., Hehre W.J., Binkley J.S., Gordon M.S., DeFrees D.J., and Pople J.A. J. Chem. Phys. 77 (1982) 3654-3665
46. 7b of parent cyclobutylidene using reliable computational methods. They also reported that singlet cyclobutylidene is predicted to have a non-classical bicyclobutane-like structure with the C1-C3 bond lengths between 1.72 and 1.85 Å.
47. Sugiyama M.H., Celebi S., and Platz M.S. J. Am. Chem. Soc. 114 (1992) 966-973