References
- Part 5 of Chemistry of Sulfonylmethylisocyanides, for Part 4 see ref. 4c
- Stetter , H. and Tillmans , V. 1972 . Chem. Ber. , 105 : 735
- van Leusen , A. M. , Boerma , G. J. M. , Helmholdt , R. B. , Siderius , H. and Strating , J. 1972 . Tetrahedron Letters , in oress. Our experimental conditions for the dehydration of N-tosyl-methylformamide are the following. A solution of POCl3 (11 ml, 0.12 mole) in dry dimethoxyethane (25 ml) is added dropwise (in 1 hr.) to a stirred suspension of the formamide (21.3 g, 0.10 mole) in a mixture of dry dimethoxyethane (150 ml) and triethylamine (70 ml) at 0–10°. After stirring for an additional 30 min. at the same temperature, ice-water (500 ml) is added. The precipitate is collected, dissolved in benzene and the water is separated. By addition of pentane to the dried (MgSO4) and charcoaled benzene solution, Ia is obtained (80–86% yield) as a near-white, odourless and stable isocyanide, which can be used for synthetic purposes without further purification
- van Leusen , A. M. , Hoogenboom , B. E. and Siderius , H. 1972 . Tetrahedron Letters , in press
- van Leusen , A. M. and Oldenziel , O. H. in press . Tetrahedron Letters ,
- Oldenziel , O. H. and van Leusen , A. M. in press . Tetrahedron Letters ,
- van Leusen , A. M. , Siderius , H. , Hoogenboom , B. E. and Daan van Leusen . unpublished
- van Leusen , A. M. , Hoogenboom , B. E. and Siderius , H. unpublished;. U. Schöllkopf and R. Schröder, Angew. Chem., 84, 289 (1972)
- An authentic sample was kindly supplied by Drs. S. Reiffers from our laboratory, who has prepared an analytically pure compound, mp. 181–182°C, by dehydration of the corresponding amide, unpublished results