Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups. It is a colourless solid that, unlike many isocyanides, is odorless. It is prepared by dehydration of the related formamide derivative. It is used in the Van Leusen reaction which is used to convert ketones to nitriles or in the preparation of oxazoles[2] and imidazoles.[3] The versatility of TosMIC in organic synthesis has been documented.[4] It is a fairly strong carbon acid, with an estimated pKa of 14 (compared to 29 for methyl tolyl sulfone), the isocyano group acting as an electron acceptor of strength comparable to an ester group.[5]
^p-Toluenesulfonylmethyl isocyanide at Sigma-Aldrich
^Keeri, Abdul Raheem; Gualandi, Andrea; Mazzanti, Andrea; Lewinski, Janusz; Cozzi, Pier Giorgio (2015-12-21). "Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones". Chemistry – A European Journal. 21 (52): 18949–18952. doi:10.1002/chem.201504362. ISSN 1521-3765. PMID 26549317.
^Hoogenboom, B. E.; Oldenziel, O. H.; van Leusen, A. M. (1977). "p-TOLYLSULFONYLMETHYL ISOCYANIDE". Organic Syntheses. 57: 102; Collected Volumes, vol. 6, p. 987.
^"Toluenesulphonylmethyl isocyanide (TOSMIC) and the van Leusen MCR". www.organic-chemistry.org. Retrieved 2017-02-28.
^van Leusen, Albert M.; van Leusen, Daan; Czakó, Barbara (2008-09-15), "p-Tolylsulfonylmethyl Isocyanide", Encyclopedia of Reagents for Organic Synthesis, John Wiley & Sons, Ltd, doi:10.1002/047084289x.rt150.pub2, ISBN 978-0471936237
TosMIC (toluenesulfonylmethyl isocyanide) is an organic compound with the formula CH3C6H4SO2CH2NC. The molecule contains both sulfonyl and isocyanide groups...
Van Leusen reaction can also be employed to form imidazoles starting from TosMIC and an aldimine. The Van Leusen Imidazole Synthesis allows the preparation...
The Van Leusen reaction is the reaction of a ketone with TosMIC leading to the formation of a nitrile. It was first described in 1977 by Van Leusen and...
α-haloketones and formamide and the Van Leusen reaction with aldehydes and TosMIC. In biomolecules, oxazoles result from the cyclization and oxidation of...
Leusen reaction pyrroles are produced by reaction of tosylmethyl isocyanide (TosMIC) with an enone in the presence of base, in a Michael addition. A 5-endo...
with surgery. It acts as a COX-2 inhibitor. Reaction of the imine with TosMIC in the presence of potassium carbonate leads to what may be viewed as 2+3...
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