A Convenient Method for the Synthesis of Sterically Hindered Aryl Isocyanates

Abstract

<jats:title>Abstract</jats:title><jats:p> Reaction of a sterically hindered aniline with a sterically non-hindered arylisocyanate produces the sterically hindered aryl isocyanate in good yields besides the urea derived from the unhindered aryl isocyanate.</jats:p>

Identification of the Side Products That Diminish the Yields of the Monoamidated Product in Metal-Catalyzed C–H Amidation of 2-Phenylpyridine with Arylisocyanates

“…An examination of extracted ion chromatograms, confirmed the presence of 1 and 3a – 7a , which were readily separated using a gradient of CH 3 CN/H 2 O containing 0.1% formic acid (Figure b). Other ions at m / z 213 and 332 provide evidence for the known phenyl isocyanate decomposition products (Scheme ), N , N′ -diphenyl urea ( 8a ), and 1,3,5-triphenyl biuret ( 9a ). , Related products and side products formed in the C–H amidation of 1 by 2b and 2c were found in the crude reactions mixtures via ESI-HRMS and LC–MS (Figures S16–S19 and Tables S2–S3).…”

“…Other ions at m/z 213 and 332 provide evidence for the known phenyl isocyanate decomposition products (Scheme 2), N,N′-diphenyl urea (8a), and 1,3,5-triphenyl biuret (9a). 25,26 Related products and side products formed in the C−H amidation of 1 by 2b and 2c were found in the crude reactions mixtures via ESI-HRMS and LC−MS (Figures S16−S19 and Tables S2−S3). 27 The formation of these side products was not reported previously.…”

Aliphatic tertiary amine catalysed urethane formation – a combined experimental and theoretical study

“…1,3, 5-Triphenylbiuret was prepared by reacting PhNCO with N, N 0 -diphenylurea. 21 1,3-Diphenyl-1,3-diazetidine-2,4-dione (PhNCO dimer) was synthesized from PhNCO by catalytic dimerization 22 and purifying the dimer by recrystallization from ethyl acetate. 1,3,5-Triphenyl-1,3,5-triazinane-2,4,6-trione (PhNCO trimer) was synthesized from PhNCO by catalytic cyclotrimerization.…”

Fragmentation of an N-Substituted One-Coordinate Phosphorus (Phosphaalkyne): Plausible Generation of Monovalent Phosphorus Species

“…Yield of supermesitylisonitrile ( 8 ) was 0.29 g (28%) as a white solid, with a mp of 113 °C (lit. 112−114 °C) …”