Bruylants

BRUYLANTS Amination Amination aR[Pg.53]

J ULIA-BRUYLANTS Cyclopropyl Carbinol Rearrangement Synthesis ot allyl halides (usually E] by rearrangement ol cyciopropyl carbirKils acid catalyzed)... 

Allyl cyanide has been found in oil of mustard 1 and has been prepared from allyl chloride and potassium cyanide,2 allyl bromide and potassium cyanide,3 allyl iodide and potassium cyanide4 and silver cyanide.5 The method described in the procedure is essentially that of Bruylants, who has shown that the yields are much better when dry cuprous cyanide is treated with allyl bromide.6... 

Fievesi L, Wolfson-Davidson E, Nagy JB, Nagy OB, Bruylants A. J Am Chem Soc 1972 94 4715-20. 

Diese schon von Wallach (3) sowie von Bruylants und Dewael (4) beob-achtete Umlagerungsreaktion 73) ist spater der Gegenstand zahlreicher Untersuchungen verschiedener Autoren gewesen. 

Using the same methodology, chiral 3-substituted 3-phenylalkanones can also be prepared34. The precursor chiral allylamines 8 were synthesized from ( )-3-phenylpropenal via the a-aminoallyl cyanide using the Bruylants reaction35. 

See also Soumillion Bruylants Bull. Soc. Chim. Belg. 1969, 78.425 Potter Tedder J. Chem. Soc., Perkin Trans. 2 1982, 1689 Aver yanov Ruban Shvets J. Org. Chem. USSR 1987, 23. 782 Aver yanov Ruban J. Org. Chem. USSR 1987,23. 1119 Raner Lusztyk Ingold J. Am. Chem. Soc. 1989, III, 3652 Ingold Lusztyk Raner Acc. Chem. Res. 1990, 23. 219-225. 

For reviews of the mechanism, sec Bruylants Feytmants-dc Mcdicis. in Palai The Chemistry of the Carbon-Nitrogen Double Bond Wiley New York, 1970, pp. 465-504 Salomaa. in Palai. Ref. 2, pt. 1. pp. 199-205. 

The method of Bruylants and Desmet 8 was similar to the foregoing. Tellurium prepared from hydrogen telluride was treated with nitric acid and the resulting dioxide separated by evaporation, calcined, and... 

Hydrogen telluride was also the starting-point in the investigation of Bruylants and Michielsen.3 The gas after careful purification was decomposed into its elements at 200° to 220° C., the tellurium weighed as such and the hydrogen oxidised to water by means of cupric oxide. The value obtained was 127-8. 

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