Rhodium-Catalyzed Anti-Markovnikov Hydrohydrazination of Terminal Alkynes with N-Alkyl- and N,N-Dialkylhydrazines was written by Fukumoto, Yoshiya;Ohmae, Akihiro;Hirano, Masaya;Chatani, Naoto. And the article was included in Asian Journal of Organic Chemistry in 2013.Product Details of 4435-14-7 This article mentions the following:
The anti-Markovnikov addition of hydrazines to terminal alkynes in the presence of [TpRh(C2H4)2]/P(2-furyl)3 (Tp=trispyrazolylborate) as a catalyst system has been developed. N-alkyl- and N,N-dialkyl-substituted hydrazines are applicable to this highly regioselective hydrohydrazination, which affords aldimine-type hydrazine derivatives In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Product Details of 4435-14-7).
2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Product Details of 4435-14-7
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts