Synthesis of Nitroso- and Dinitroso Compounds by Reaction of Nitrosyl Benzoate and Dinitrosylterephthalate with Tetrasubstituted Alkenes

Thomas R. Sharpe; Brian G. Gowenlock

doi:10.1055/s-2006-942392

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Synthesis of Nitroso- and Dinitroso Compounds by Reaction of Nitrosyl Benzoate and Dinitrosylterephthalate with Tetrasubstituted Alkenes

Thomas R. Sharpe^a,c, Brian G. Gowenlock*^b
^a P. O. Box 7288, Wilmington, Delaware, DE 19803, USA
^b Riccarton, 5 Roselands, Sidmouth, Devon EX10 8PB, UK
e-Mail: Brian.gowenlock@btinternet.com;
^c Explosives Department, E. I. Du Pont de Nemours & Company, Du Pont Experimental Station, Wilmington, Delaware, DE 19898, USA

Abstract

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Abstract

The reaction of nitrosyl benzoate with tetrasubstituted alkenes at 0 °C produces monomeric C-nitroso compounds in high yields. Similarly, the reaction of dinitrosyl terephthalate with 2,3-dimethylbut-2-ene affords a monomeric dinitroso compound. Extension to other nitrosyl esters gives similar high yields.

Key words

nitrosyl esters - tetrasubstituted alkenes - cycloalkenes - nitroso compounds - dinitroso compounds

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References

1 Gowenlock BG. Richter-Addo GB. Chem. Rev. 2004, 104: 3315

2 Gowenlock BG. Richter-Addo GB. Chem. Soc. Rev. 2005, 34: 797

3 Hamann HC. Swern D. J. Am. Chem. Soc. 1968, 90: 6481

4 Sharpe TR. Euchem Conference on C-Nitrosocompounds; Newbattle: Scotland, September 1969

5 Mason J. van Bronswijk W. Winter JG. J. Chem. Soc., Perkin Trans. 2 1977, 469

6 Cameron M. Gowenlock BG. Vasapollo G. Chem. Soc. Rev. 1990, 19: 355

7 Lee J. Chen L. West AH. Richter-Addo GB. Chem. Rev. 2002, 102: 1019

8 Olah GA. Kuhn SJ. Flood SH. Hardin BA. J. Am. Chem. Soc. 1964, 86: 1043