Radical cyclizations of 2-(ω-haloalkylthio)enones to thiapolycycloalkanones

Author:

Ponaras Anthony A,Zaim Ömer

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference24 articles.

1. Ponaras, A. A.; Zaim, Ö. Tetrahedron Lett. 1993, 34, 2879.

2. Preparation of 6s: rxn of 2-bromo-2-cyclohexen-1-one with potassium 2-iodobenzyl thiolate in THF (cf., Fujisawa, T.; Sakai, K.; Shirokata, H.; Fukushima, A. (Sagami Chemical Research Center) Jpn. Kokai Tokkyo Koho JP 54,088,210 (1977) Chem. Abstr. 1979, 92, 76093c. Preparation of 10: heating 1,2-cyclohexanedione and 3-chloro-1-propanethiol in benzene (cat. TsOH) under a Dean–Stark trap, followed by treatment with sodium iodide in acetone. Preparation of 13, 14, 17 and 21: rxn of 2,3-epoxycyclohexanone with the appropriate sodium thiolate in ethanol (cf., Tobias, M. A.; Strong, J. G.; Napier R. P. J. Org. Chem. 1970, 35, 1709. Preparation of 18: rxn of 2,3-epoxycyclohexanone with sodium 2-hydroxymethyl benzenethiolate in ethanol, followed by treatment with chlorotrimethylsilane/HMDS, followed by treatment with iodotrimethylsilane.

3. For a review of thiadecalins, see: Klimenko, S. K.; Stolbova, T. V. Usp. Khim. 1985, 54, 803.

4. (a) Claus, P. K.; Rieder, W.; Vierhapper, F. W. Mh. Chem. 1978, 109, 609.

5. (b) Vierhapper, F. W.; Willer, R. L. J. Org. Chem. 1977, 42, 4024.

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