Abstract
IN 1913 Sommelet1 observed that when the quaternary compound from benzyl chloride and hexamine is heated in water, or in aqueous alcohol, it is converted in good yield to benzaldehyde. This reaction has become general for the preparation of aromatic aldehydes. Sommelet isolated methylamine as a by-product, and suggested that the reaction mechanism is such that the quaternary compound first hydrolyses to methylene-benzylamine, which then isomerizes to benzylidene methylamine ; and that the benzaldehyde and methylamine are derived from the hydrolysis of the latter :
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References
Sommelet, M., C.R. Acad. Sci., Paris, 157, 852 (1913).
Graymore, J., and Davies, D. R., J. Chem. Soc., 293 (1945).
Plöchl, J., Ber., 21, 2117 (1888). Werner, E. A., J. Chem. Soc., 111, 844 (1917).
Leuckart, B., Ber., 18, 2341 (1885). Wallach, O., Ann., 343, 60 (1905).
Ingersoll, A. W., "Org. Synth. Coll.", 2, 503.
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ANGYAL, S., RASSACK, R. The Sommelet Reaction. Nature 161, 723–724 (1948). https://doi.org/10.1038/161723b0
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DOI: https://doi.org/10.1038/161723b0
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