Novel differences between the solid state and solution phase photochemistry of 1,2-cyclodecanedione

Tetrahedron Letters

Volumn 38, Issue 37, 1997, Pages 6549-6552

  Olovsson, Gunnar ^a   Scheffer, John R ^a   Trotter, James ^a   Wu, Chung Hsi ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DIKETONE;

ARTICLE; LIQUID; PHOTOCHEMISTRY; PHOTOLYSIS; SOLID STATE;

EID: 0030755325     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01657-2     Document Type: Article

References (12)

1. Gudmundsdottir, A.D.; Lewis, T.J.; Randall, L.H.; Scheffer, J.R.; Rettig, S.J.; Trotter, J.; Wu, C-H. J. Am. Chem. Soc. 1996, 118, 6167.
2. Urry, W.H.; Trecker, D.J.; Winey, D.A. Tetrahedron Lett. 1962, 609.
3. (a) Allinger, N.L. Org. Syntheses 1964, 4, 840;
4. (b) Gream, G.E.; Worthley, M.S. Tetrahedron Lett. 1968, 3319
5. 1/a; a = 13.670(3), b = 5.232(1), c = 14.521(3) Å; β = 114.82(2)°; Z = 4; R = 6.6%.
6. Wagner, P.J.; Zepp, R.G.; Liu, K-C.; Thomas, M.; Lee, T-J.; Turro, N.J. J. Am. Chem. Soc. 1976, 98, 8125.
7. Compound 3 was synthesized by converting cyclooctanone into 2-allylcyclooctanone (Crandall, J.K.; Magaha, H.S.; Henderson, M.A.; Widener, R.K.; Tharp, G.A. J. Org. Chem. 1982, 47, 5372) followed by ozonolysis and reductive workup.
8. Wagner, P.J.; Park, B-S.; Sobczak, M.; Frey, J.; Rappoport, Z. J. Am. Chem. Soc. 1995, 117, 7619.
9. Keto-aldehyde 3 also does not absorb at λ > 340 nm, thus ruling out its conversion to 2a and/or 2b.
10. 1
11. Precedent for this type of process can be found in Rubin, M.B. Top. Curr. Chem. 1985, 129, 1.
12. The crystallographic γ-H to acyl carbon distances in 1 are 2.82 and 2.83 Å. These distances are below the sum of the van der Waals radii for carbon and hydrogen (2.90 Å). Carbenic insertions of this type are, to the best of our knowledge, unprecedented.