Photolytic double decarbonylation route to highly substituted indenes and benzene derivatives

Tetrahedron

Volumn 52, Issue 7, 1996, Pages 2481-2488

  Thomas, Abraham ^a   Anilkumar, Gopinathan ^a   Nair, Vijay ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; INDENE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOTOCHEMISTRY; PRIORITY JOURNAL;

EID: 0030063021     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01069-6     Document Type: Article

References (15)

1. Farnia, G.; Marcuzzi, F.; Melloni, G.; Sandona, G.; Zucca, M. V. J. Am. Chem. Soc. 1989, 111, 918 and relevant references cited therein.
2. Marcuzzi, F.; Azzena, U.; Melloni, G. J. Chem. Soc. Perkin Trans. I 1993, 2957.
3. (a) Nair, V.; Kumar, S.; Williard, P. G. Tetrahedron Lett., 1995, 36, 1605.
4. (b) Nair, V.; Kumar, S.; Rath, N. P.; Morton G. O. Chemistry Lett., 1995, 383;
5. Nair, V.; Kumar, S.; Anilkumar, G; Nair, J. S. Tetrahedron, 1995, 51, 9155.
6. a) For earlier work see: Friedrichsen, W.; Betz, M.; Buldt, E.; Jurgens, H. J.; Schmidt, R.; Schwarz, I.; Visser, K. Liebigs. Ann. Chem. 1978, 440.
7. b)For review see; Finley, K.T. in "The Chemistry of quinanoid compounds" Vol.2, (Ed). Patai, S,; Rappoport, Z, John Wiley, Chichester, 1988, 537.
8. For an elegant application of this methodology to the synthesis of cyclooctatetraene, see: (a) Wells, G.; Hanzawa, Y.; Paquette, L. A. Angew. Chem. Int. Ed. Engl. 1979, 18, 544. For a recent report on bisdecarbonylation see:
9. (b) Kim, S. S; Yu, Y.H; Shim, S. C; Cho, I. H. Tetrahedon Lett. 1994, 35, 9039.
10. The utility of photoextrusion in synthesis is well established. For an excellent review, see: (a) Givens, R. S. 'Organic Photochemistry (Ed.) Padwa, A., Marcel Dekker,1981, Vol. 5, Chapter 3, p 273.
11. 3CN as solvent improved the solubility of the adduct, but lowered the yield of photoproducts and only partial conversion was observed. Undesirable side reactions were also observed under this conditions.
12. DDQ reaction failed to give the dehydrogenated product. It is not clear why the methyl substitution in the exomethylene carbon affects the success of this reaction.
13. Interconversions of geometrical isomers (E&Z) of benzofulvenes is well established: (see ref. 6).
14. Liao, C. C.; Lin, H. S. J. Chin. Chem. Soc. 1986, 33, 73.
15. Nanosecond laser flash photolysis of 7c was carried out using the 355 nm out put of a Quanta-Ray GCR-12 series Nd: YAG laser (pulse width 6 ns). Transient absorption was monitored from 300 nm to 800 nm using an Applied Physics laser kinetic spectrometer. A deoxygenated solution of 7c (under argon) in cyclohexane having an absorbance of 0.226 at 355 nm was used for the experiment. Under these conditions, no transient species were observed. The authors thank Mr. C. S. Rajesh of the Photochemistry Research Unit for this experiment.