The reaction of 1,3,5-trinitrobenzene with methoxide and hypochlorite ions

Journal of Organic Chemistry

Volumn 61, Issue 4, 1996, Pages 1551-1554

  Mallory, Frank B ^b   Amenta, Donna S ^a,b   Mallory, Clelia W ^c   Cheung, Jih Jen Joy Chiang ^b  

^a JAMES MADISON UNIVERSITY   (United States)

^b BRYN MAWR COLLEGE   (United States)

^c UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0011204841     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951784f     Document Type: Article

References (25)

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9. A small amount (3% yield) of 3,5-dmitroanisole also is obtained under these reaction conditions. This compound is the major product from the reaction of 1,3,5-trinitrobenzene (1) with methoxide ion in methanol solution in the absence of hypochlorite ion. (a) Lobry de Bruyn, C. A. Recl. Trav. Chim. Pays-Bas 1890, 9, 208. (b) Reverdin, F. Organic Syntheses; Wiley: New York, 1932; Collect. Vol. I, p 219. (c) Gold, V.; Rochester, C. H. J. Chem. Soc. 1964, 1692.
10. A small amount (3% yield) of 3,5-dmitroanisole also is obtained under these reaction conditions. This compound is the major product from the reaction of 1,3,5-trinitrobenzene (1) with methoxide ion in methanol solution in the absence of hypochlorite ion. (a) Lobry de Bruyn, C. A. Recl. Trav. Chim. Pays-Bas 1890, 9, 208. (b) Reverdin, F. Organic Syntheses; Wiley: New York, 1932; Collect. Vol. I, p 219. (c) Gold, V.; Rochester, C. H. J. Chem. Soc. 1964, 1692.
11. A small amount (3% yield) of 3,5-dmitroanisole also is obtained under these reaction conditions. This compound is the major product from the reaction of 1,3,5-trinitrobenzene (1) with methoxide ion in methanol solution in the absence of hypochlorite ion. (a) Lobry de Bruyn, C. A. Recl. Trav. Chim. Pays-Bas 1890, 9, 208. (b) Reverdin, F. Organic Syntheses; Wiley: New York, 1932; Collect. Vol. I, p 219. (c) Gold, V.; Rochester, C. H. J. Chem. Soc. 1964, 1692.
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15. The conversion of 14 to 15 has a close parallel in the reported formation of 1,2-naphthoquinone from 1-chloro-1-nitro-2-keto-1,2-dihydronaphthalene in chloroform solution by the thermally induced loss of nitrosyl chloride. Perrin, C. L. J. Org. Chem. 1971, 36, 420.
16. Five permutations are conceivable for the sequence of these six steps: M-C-M-C-M-C, M-C-M-M-C-C, M-M-C-C-M-C, M-M-C-M-C-C, and M-M-M-C-C-C.
17. 6 by way of base-induced ring-opening followed by a series of chlorination and fragmentation reactions. equation presented
18. Mallory, F. B. J. Chem. Educ. 1962, 39, 261.
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20. Schouten, A. E. Recl. Trav. Chim. Pays-Bas 1937, 56, 541.
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24. (d) Terrier, F.; Millot, F.; Schaal, R. J. Chem. Soc., Perkin Trans. 2 1972, 1192.
25. We thank Professor David R. Dalton of Temple University for these measurements.