By Henderson L.J.
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Extra resources for The Fitness of the Environment
Sample text
On irradiation with ultraviolet light, cyclohexanone thioacetal produces the radical (36),which gives intermediary cyclohexanethione by the elimination of a HSCHzCHz radical from the side chain; this thione readily dimerizes t o afford the spiro-1,3-dithi- (37) R . M. , p. 30. Wiley (Interscience), New York, 1967. 52 Acheson,51 p. 9. 53 G. Stefanovic, L. Lorenc, R. I. Mamuzid, and M. L. Mihailovid, Tetmhedrom 6, 304 (1959). 54 I. M. Goldman, J. K. Larson, J. R. Tretter, and E. G. Andrews, J . Amer.
Cramer, Angew Chem. Int. Ed. Engl. 5, 173 (1966); (b)M. Ikehara, Kagaku no Ryoiki 25, 300 (1971). 172 40 A. ALBERT AND H. YAMAMOTO [Sec. C. Pterorhodine (1 13b)lS1and drosopterin (133)ls2are naturallyoccurring dimeric pteridines ; the former was synthesized from xanthopterin and acetone or acetaldehyde in the presence of ammonium sulfate or hydrogen peroxide, 136 and the latter from 7,8-dihydropterin and /I-keto-ahydroxybutyric acid. The complete structure of a large peptide macrocycle bearing two 2-quinoxalinyl substituents has been elucidated by Prelog and co-workers.
I57 J. Thesing, Ber. 87, 692 (1954). 158 G. 0. Burr and R. A. Gortner, J. Amer. Chem. SOC. 46, 1224 (1924). 159 R. A. Heacock and S. Kakppirek, Advan. Heterocycl. Chem. 10, 43 (1969). 155 Sec. 1 HETEROCYCLIC OLIGOMERS 37 be made. 160 have prepared compound 130 by the Grignard reaction of “thienylmagnesium bromide with methyl 3-(1-methylpiperidyl)carboxylate, followed by dehydration of the resulting carbinol with 10 N hydrochloric acid; 130, known as Asverin, is used as an antitussive. lB1The 2,2’-thenils (79;X = S , R=Fi-F, or 5-adamantyl) were made by the reaction of two molecules of the corresponding 2-lithiothiophene with dimethyl oxalate.