87282-20-0

Upstream product

• 10442-39-4 tetra-n-butylammonium cyanide 
• 4222-25-7 3-bromo-3-phenyl-3H-diazirine 

Downstream Products

• 15036-26-7 1-phenyl-2,2,3,3-tetramethylcyclopropanecarbonitrile 
• 90284-46-1 (2R,3R)-2,3-Dimethyl-1-phenyl-cyclopropanecarbonitrile 
• 90284-46-1 (1S,2S,3R)-2,3-Dimethyl-1-phenyl-cyclopropanecarbonitrile 
• 90364-93-5 (1R,2R,3S)-2,3-Dimethyl-1-phenyl-cyclopropanecarbonitrile 

Relevant academic research and scientific papers

Nitrenic reactivity of diazirines

Butyl 3-bromo-3H-diazirine-3-carboxylate (7) and 3-bromo-3-phenyl-3H- diazirine (17) exhibit nitrenic reactivity with phenylmagnesium bromide or tetrabutylammonium cyanide. The formation of several N,N′-disubstituted amidines is attributed to the intermediacy of 1-phenyl or 1-cyano-1H-diazirines possessing a singlet imidoylnitrene character at the N2 atom. Most notably, the reaction of 7 with PhMgBr in diethyl ether affords 2-hydroxy-2,2,N- triphenylacetamidine (9) and 2-methyl-5,5-diphenyl-4-phenylamino-2,5- dihydrooxazole (10) as products derived from nitrene insertion to the ether α-C-H bond.

NOVEL PREPARATION OF CYANOPHENYLCYCLOPROPANES VIA CYANOPHENYLCARBENE

Bromophenyldiazirine (1) is converted to cyanophenyldiazirine (2) upon stirring with tetra-n-butylammonium cyanide.Photolysis of 2 affords cyanophenylcarbene which is readily trapped by alkenes to yield cyanophenylcyclopropanes.