Aryl ones are synthesized using tert-butyl nitrite and a substituted trimethylsilane, while vinylic ones are synthesized from allenes that have an electron withdrawing group across from the site of addition. The classic alkyl synthesis of these is the Dutt-Wormall reaction, which uses a sulfonamide, and they frequently rearrange to isocyanates. These compounds also provide the easiest way to aminate a compound, by reacting this functional group's sodium salt under SN2 conditions and then reducing the product with lithium aluminum hydride. For 10 points, name this functional group, which, taken alone, isoelectronic with carbon dioxide, a series of three double-bonded 
Aryl ones are synthesized using tert-butyl nitrite and a substituted trimethylsilane, while vinylic ones are synthesized from allenes that have an electron withdrawing group across from the site of addition. The classic alkyl synthesis of these is the Dutt-Wormall reaction, which uses a sulfonamide, and they frequently rearrange to isocyanates. These compounds also provide the easiest way to aminate a compound, by reacting this functional group's sodium salt under SN2 conditions and then reducing the product with lithium aluminum hydride. For 10 points, name this functional group, which, taken alone, isoelectronic with carbon dioxide, a series of three double-bonded atoms of nitrogen.
Aryl ones are synthesized using tert-butyl nitrite and a substituted trimethylsilane, while vinylic ones are synthesized from allenes that have an electron withdrawing group across from the site of addition.
azide