Convenient synthesis of 2-thionaphthylmethyl isocyanide: a useful reagent for methyl isocyanide transfer

Ranganathan, S. ; Singh, W. P. (1988) Convenient synthesis of 2-thionaphthylmethyl isocyanide: a useful reagent for methyl isocyanide transfer Tetrahedron Letters, 29 (12). pp. 1435-1436. ISSN 0040-4039

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4039(00)80317-2

Abstract

The crystalline 2-thionaphthylmethyl isocyanide (1̲), prepared from the novel N-(formamidomethyl)-N-benzyl morpholinium iodide (2̲ ), via transfer of elements of CH2NHCHO, is totally devoid of pervasive odour. The cyclo-addition of the conjugate base of (1̲ ) to nitriles followed by desulfurization, under very mild conditions, provides an attractive route to imidazoles.

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