Summary and conclusions
Three new reactions of fatty isocyanides were discovered and are summarized below.
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a)
With halogens, products of the type (RNCX)n were isolated; this differs from the aromatic or short-chain isocyanides which form RNCX2 under similar conditions.
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b)
With alkylating agents, such as methyl chloride or ethyl sulfate, the fatty isocyanides formed quaternary-like surface-active derivatives. This type of reaction has not been reported previously.
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c)
With acid chlorides, the following type of structures were formed:
$$\left( {\begin{array}{*{20}c} {R''C = O} \\ | \\ {R'N = C} \\ \end{array} } \right)^ + Cl^ - $$this differs from the aromatic or short-chain isocyanides which are reported to form
under similar conditions.
In reactions of fatty isocyanides with alkylating agents and with acid chlorides evidence was presented to indicate that addition occurred at the nitrogen of the isocyanide group. These are the first examples in the literature of such reactions by isocyanides.
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References
Gautier, A., Ann.,151, 239 (1866).
Nef, J. V.,ibid.,,270, 274 (1892).
Nef, J. V.,ibid.,,287, 265 (1895).
Passerini, M., Gazz. chim. ital.,56, 365 (1926).
Passerini, M.,ibid.,,53, 410 (1923).
Gilman, H., “Organic Chemistry,” 2nd ed., vol. 2, pp. 1907–1908, John Wiley and Sons, New York, 1947.
Whitmore, F. C., “Organic Chemistry,” 1st ed., pp. 505–506, D. Van Nostrand Company Inc., 1938.
Baker, R. H., and Stanosis, D., J. Am. Chem. Soc.,73, 699 (1951).
McBride, J. J., and Berchell, H. C.,ibid.,,74, 5247 (1952).
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Jungermann, E., Smith, F.W. New reactions of long-chain isocyanides. J Am Oil Chem Soc 36, 388–392 (1959). https://doi.org/10.1007/BF02639612
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DOI: https://doi.org/10.1007/BF02639612