On the purported synthesis of a bicyclo[2.2.1]heptene diester by reaction of diazomethane with dimethyl 1,3-cyclohexadiene-1,4-dicarboxylate
Author:
Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference7 articles.
1. Guha, P. C.; Hazra, G. D. J. IndianInst. Sci. 1939, 22A, 263; Chem. Abstr.1940, 34, 2822;4Beilstein1971, 9, III, 4044b.
2. A general method for alkylating 2(5H)-furanones; reduction of products to 3-, 2,3-, and 3,4-substituted furans
3. Une application du cycle pyrazoline à la lactamisation et à la formylation de 6H thiazines-1,3
4. Compound 6a: colorless oil. 1H NMR (400 MHz, CDCl3): 1.33 (t, 1H, J=4.8 Hz), 1.67 (dd, 1H, J=9.3, 4.3 Hz), 1.93 (m, 1H), 1.96–2.02 (m, 2H), 2.27 (m, 1H), 2.68 (m, 1H), 3.72 (s, 3H), 3.74 (s, 3H), 7.28 (m, 1H) ppm. 13C NMR (100 MHz, CDCl3): 18.96 (t), 19.55 (t), 20.08 (t), 21.48 (d), 28.29 (s), 51.62 (q), 52.08 (q), 126.98 (s), 139.26 (d), 167.01 (s), 174.61 (s) ppm. MS (API-ES): m/z, 233 (M++23). The observed UV absorption of 6a is in good agreement with the electronic spectra reported for related cyclopropylacrylic esters by: Jorgenson, M. J.; Leung, T. J. Am. Chem. Soc. 1968, 90, 3769.
5. cis-Cyclopentane-1,3-dicarboxylic acid, mp 120–121°C, was prepared for reference by Dr. Jiong Lan following the procedure of: Hronowski, L. J. J.; Szarek, W. A. Can. J. Chem. 1988, 66, 61.
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1. Preparation of Conformationally Constrained α2 Antagonists:The Bicyclo[3.1.0]hexane Approach;European Journal of Organic Chemistry;2005-08
2. From 3,4-Dinitrothiophene to Nitrocyclopropanes and 1,1′-Dinitro-1,1′-bi(cyclopropyl) Compounds;European Journal of Organic Chemistry;2002-04
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