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Timestamp: 2019-04-20 00:37:33+00:00

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Physical Data: colorless, mobile liquid; bp 22 °C/70 mmHg,2 2-3 °C/14 mmHg;3 d 1.24 g cm-3.
Solubility: miscible with common organic solvents.
Handling, Storage, and Precautions: unstable and explosive upon heating.2,4 Isolation or distillation is not recommended unless extreme care is taken; freshly prepared solutions should be employed. Controlled thermolysis at ~60 °C leads to N-oxides, tetranitromethane,2 and a yellow oil.5 Highly acidic; avoid skin contact. Reactions should be conducted in a well-ventilated fume hood.
Acetyl nitrate reacts rapidly with thioethers and disulfides to give sulfoxides, even at temperatures far below 0 °C; no further oxidation to sulfones occurs, even with an excess of reagent, and yields are near quantitative (eqs 7 and 8).22 With sulfides that are susceptible to Pummerer-type reactions with Ac2O, the use of Benzoyl Nitrate is preferred.
1. (a) FF 1968, 1, 13. (b) Hoggett, J. G.; Moodie, R. B.; Penton, J. R.; Schofield, K. Nitration and Aromatic Reactivity; Cambridge: London, 1971; p 76. (c) Taylor, R. Electrophilic Aromatic Substitution; Wiley: New York, 1990, p 269.
2. Pictet, A.; Khotinsky, E. CB 1907, 40, 1163.
3. Farbw. Hoechst, Ger. Patent 849 405, 1952 (CA 1953, 47, 4899).
4. (a) König, W., AG 1955, 67, 157. (b) Brown, T. A.; Watt, J. A. C. Chem. Br. 1967, 3, 504. (c) Gilbert, E. E. Chem. Eng. News 1980, 58 (40), 5.
5. Chrétien, A.; Boh, G. CR(C) 1945, 220, 822.
6. (a) Chédin, J.; Fénéant, S. CR(C) 1949, 229, 115. (b) Tsvetkov, V. G.; Shmakov, V. A.; Sopin, V. F.; Ivanov, A. V.; Ikonnikov, A. A.; Marchenko, G. N. JGU 1989, 59, 1220.
7. Folsum, H. E.; Castrillón, J. SC 1992, 22, 1799.
8. Olah, G. A.; Lin, H. C.; Olah, J. A.; Narang, S. C. PNA 1978, 75, 1045.
9. Burton, H.; Praill, P. F. G. JCS 1955, 729.
10. Hayashi, E.; Inana, K.; Ishikawa, T. YZ 1959, 79, 972.
11. Velichko, L. I.; Kachurin, O. I.; Balabanov, E. Yu. UKZ 1983, 49, 1293 (CA 1984, 100, 138 725).
12. Velichko, L. I.; Kachurin, O. I.; Balabanov, E. Yu. UKZ 1988, 54, 171 (CA 1989, 110, 38 364).
13. Sifniades, S., JOC 1975, 40, 3562.
14. Bordwell, F. G.; Garbisch, E. W., Jr. JACS 1960, 82, 3588.
15. Borisenko, A. A.; Nikulin, A. V.; Wolfe, S.; Zefirov, N. S.; Zyk, N. V. JACS 1984, 106, 1074.
16. Kolb, V. M.; Darling, S. D.; Koster, D. F.; Meyers, C. Y. JOC 1984, 49, 1636.
17. (a) Drefahl, G.; Crahmer, H. CB 1958, 91, 745; (b) Drefahl, G.; Crahmer, H. CB 1958, 91, 750.
18. Zyk, N. V.; Nikulin, A. V.; Ugrak, B. I.; Borisenko, A. A.; Zefirov, N. S. ZOR 1985, 21, 1189 (CA 1986, 104, 186 032).
19. Liepins, E.; Zolotoyabko, R. M.; Stradins, J.; Trusule, M.; Venters, K. KGS 1980, 741 (CA 1980, 93, 220 008).
20. Bonner, T. G. JCS 1959, 3908.
21. Boyer, J. H.; Pillai, T. P.; Ramakrishnan, V. T. S 1985, 677.
22. Louw, R.; Vermeeren, H. P. W.; van Asten, J. J. A.; Ultée, W. J. CC 1976, 496.

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