Sodium trichloroac

C6o reacts with diazomethane to yield fulleroids [97,99,100,234], Carbene generated from the thermolysis of precursors such as diazirines, sodium trichloroac-etate, cyclopropene, oxadiazole, and tosylhydrazone [60,235] adds onto C6o leading to methanofullerenes [12,15,236], Recently, Akasaka et al. described the photochemical reaction of diazirine with C6o [237], Irradiation of a benzene solution of 2-adamantane-2,3 -[3H]-diazirine 58 and C6o with a high pressure mercury lamp (cutoff <300 nm) at 15°C in a Pyrex tube resulted in the formation of mixture of the isomers 59a and 59b in a ratio of 51/49 (Scheme 24). 

In the above cases, dichlorocarbene was generated from chloroform under liquid-liquid phase transfer catalytic conditions. Alternatively, sodium trichloroac-etate was also used as the precursor of dichlorocarbene as shown by the 6 -> 7 transformation (Scheme 3)[16, 18]. 

Amides can also be deacylated by partial reduction. If the reduction proceeds only to the carbinolamine stage, hydrolysis can liberate the deprotected amine. Trichloroac-etamides are readily cleaved by sodium borohydride in alcohols by this mechanism.237 Benzamides, and probably other simple amides, can be removed by careful partial reduction with diisobutylaluminum hydride (see Section 5.3.1.1).238... 

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