Allenyl(vinyl)methane photochemistry. Photochemistry of 4,4,7-trimethyl-5-phenyl-2,5,6-octatrienate derivatives

Tetrahedron Letters

Volumn 38, Issue 9, 1997, Pages 1581-1584

  Tsuno, Takashi ^a   Hoshino, Hidetaka ^a   Sugiyama, Kunio ^a  

^a NIHON UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; PYRAN; VINYL DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ISOMERISM; PHOTOCHEMISTRY; PHOTOLYSIS; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

EID: 0031550809     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00117-2     Document Type: Article

References (19)

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3. b) idem Chem. Lett. 1991, 503.
4. 3. For reports for the multiplicity control of acyclic divinylmethanes, see Ref. 2a.
5. 4: 328.1675.
6. 5. The allenic aldehyde was prepared from the reaction of 3-methyl-1-phenyl-1-butyne-3-ol with isobutyraldehyde in the presence of TsOH in benzene.
7. 6. Lehnert. W. Tetrahedron 1973, 29, 635.
8. 4: 328.1675.
9. -1), R = 0.0482, Rw = 0.0804 for 5033 unique reflections.
10. 9b) a) Fujita, K.; Matsui, K.; Shono, T. J. Am. Chem. Soc. 1975, 97, 6256;
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12. 10. Recently, "the rule of five" for the intramolecular [2+2] cycloaddition of cycloalkenones with terminal alkenes has been proved by a biradical trapping experiment using hydrogen selenide. Maradyn, D. J.; Weedon, A, C. J. Am. Chem. Soc. 1995, 117, 5359.
13. 11. Crimmins, M. T. Chem. Rev. 1988, 88, 1453; Brian, T.; McMurry, H.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811; Srinivasan, R.; Carlough, K. H. J. Am. Chem. Soc. 1967, 89, 4932.
14. 11. Crimmins, M. T. Chem. Rev. 1988, 88, 1453; Brian, T.; McMurry, H.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811; Srinivasan, R.; Carlough, K. H. J. Am. Chem. Soc. 1967, 89, 4932.
15. 11. Crimmins, M. T. Chem. Rev. 1988, 88, 1453; Brian, T.; McMurry, H.; McKenna, B. J. Chem. Soc., Perkin Trans. 1, 1991, 811; Srinivasan, R.; Carlough, K. H. J. Am. Chem. Soc. 1967, 89, 4932.
16. 12. We confirmed that the biradical intermediate for the intramolecular [2+2] cycloaddition of allenyl(vinyl)methane is a cyclopenta-1,3-diyl radical by the photochemistry of methyl 4,4,7-trimetyl-2,5,6-octatrienate in the presence of hydrogen selenide. Tsuno, T.; Sugiyama, K. unpublished result.
17. 13. MO calculation was performed using UHF PM3 method of Mac Spartan Plus of Wavefunction, Inc.
18. 14. Sugiyama. K.; Yoshida, M.; Tsuno. T. Heterocycles 1994, 38, 1721.
19. 15. For review of photochemistry of bichromophoric molecules, see: De Schryver, F. C.; Bones, N.; Put, J. Advances in Photochemistry; Pitt, Jr. J. N.; Hammond, G. S.; Gollnick, K. Eds.; John Wiley and Sons, Inc.: New York, 1977, Vol. 10, pp. 359-465.