Reactions of acyl nitroso compounds with amines: Production of nitroxyl (HNO) with the preparation of amides

Tetrahedron Letters

Volumn 37, Issue 52, 1996, Pages 9287-9290

  Atkinson, Robert N ^a   Storey, Bernadette M ^a   King, S Bruce ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; NITROUS OXIDE;

ARTICLE; DRUG SYNTHESIS; GAS CHROMATOGRAPHY; REACTION ANALYSIS;

BETULACEAE;

EID: 0030599654     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)82943-7     Document Type: Article

References (17)

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11. 9. Sklarz, B.; Al-Sayab, A.F. J. Chem. Soc. 1964, 1318-1320.
12. 2 (3 × 25 mL), the organic layers combined, dried over sodium sulfate, filtered and concentrated to give a residue which was purified by silica gel flash chromatography to give (0.152 g, 65%) of N-benzylbenzamide.
13. 2O.
14. 12. (a) Keck, G.E.; Webb, R.R.; Yates, J.B. Tetrahedron 1981, 37, 4007-4016.
15. (b) Horsewood, P.; Kirby, G.W.; Sharma, R.P.; Sweeny, J.G. J. Chem. Soc. Perkin Trans. I 1981, 1802-1806.
16. 13. Kirby, G.W.; Sweeny, J.G. J. Chem. Soc. Perkin Trans. I 1981, 3250-3254.
17. 14. General Procedure-In a 4 in. sealed tube, cycloadduct 2 (0.219 g, 1.09 mmol) and benzylamine (0.13 mL, 1.19 mmol) were dissolved in toluene (15 mL) and heated to 80 °C. After 20 h, the solution was cooled to room temperature and concentrated to provide a residue which was purified by flash chromatography to give (0.202 g, 88 %) of N-benzylbenzamide.