4-nitrobenzyl isocyanide

Synthetic applications of organosulfur reagents are expanding rapidly. Stable sulfuranes are included for the first time in BIS[2,-2,2-TRIPLUORO-l-PHENYL-l-(TRIFLUOROMETHYL)ETHOXY] diphenyl SULFURANE and DIETHYLAMINOSULFUR TRI-FLUORIDE. The latter is used to transform an alcohol to a fluoride in p-NITROBENZYL FLUORIDE. The direct homologation of a ketone to a nitrile by use of p-TOLYLSULFONYLMETHYL ISOCYANIDE is illustrated in 2-ADAMANTANECARBONITRILE. Reagents with... 

The transformation of secondary amides in the presence of the /Mactam ring has also been achieved by N-nitrosation of amides followed by thermal decomposition to esters, which were in turn hydrolyzed to the corresponding acids. Diphenyl-methyl isocyanide [14] and 4-nitrobenzyl isocyanide (PNBNC) [15] have been sue-... 

Hatanaka and co-workers found that carbapenem derivatives were readily available by means of an Ugi-4CR between 3-aminoglutaric acid mono-t-butyl ester, formaldehyde, and 4-nitrobenzyl isocyanide that gave the /l-lactam 156, which was converted into the 4-nitrobenzyl ester 157. The subsequent stereoselective Dieckmann condensation allowed the preparation of the 2-oxocarbapenem derivative 158 (Scheme 2.57) [87]. 

When 4-nitrobenzyl isocyanide reacts with an arylsulfenyl chloride it is converted into an A -(4-nitrobenzyl)-S-arylisothiocarbamoyl chloride. In the presence of triethylamine a solution containing the 1,3-dipolar species (26) is obtained. If (26) is generated in the presence of ethyl cyanoformate, cycloaddition gives an imidazole (Scheme 4,2.12) [37]. Reactions are performed at 60°C in the presence of a large excess of the dipolarophile, and yields are reported in the range 38-50%. 

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