Paul Juvvik

One-pot synthesis of secondary or tertiary amines from alcohols and amines via alkoxyphosphonium salts

Abstract Secondary or tertiary amines may be prepared from primary alcohols and primary or secondary amines by treating triphenylphosphine with N-bromosuccinimide (NBS) in the presence of the alcohol at low temperature, followed by addition of the amine and heating for about 1 h. The yield of amine is good to fair, decreasing sharply with sterically congested alcohols and starting amines.

A NEW METHOD FOR THE CONVERSION OF ALCOHOLS INTO ALKYL IODIDES

Abstract Treatment of a series of alcohols with triphenylphosphine and cyanogen iodide (a positive halogen source) affords the corresponding alkyl iodides in good yields.

HYDRAZONES FROM YLIDES AND DIAZONIUM SALTS: A CONVENIENT SPOT TEST FOR STABILIZED YLIDES OF PHOSPHORUS, ARSENIC, AND SULFUR

Abstract The reactions of a series of stabilized ylides of phosphorus, arsenic and sulfur with 2,4-dinitrobenzenediazonium tetrafluoroborate are described. The reaction courses, leading either to azo-onium salts (II), azo-onium ylides (III), formazans (IV) or hydrazones (VI), are discussed. The formation of hydrazone, which constitutes a new reaction of stabilized ylides, is interpreted in terms of stability of the transition state and of the hydrazone carbanion formed in the hydrolytic decomposition of (II) and (III). The spot test depends on the specific colour produced by the hydrazone in basic conditions, and permits detection of many stabilized ylides in concentrations down to 0.3–0.5 μg/μl.