The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《α-Hydroxy-Tetrazoles as Latent Ethynyl Moieties: A Mechanistic Investigation》. Authors are Quinodoz, Pierre; Wright, Karen; Drouillat, Bruno; Kletskii, Mikhail E.; Burov, Oleg N.; Lisovin, Anton. V.; Couty, Francois.The article about the compound:4-Chloro-4′-ethynyl-1,1′-biphenylcas:57399-11-8,SMILESS:C#CC1=CC=C(C2=CC=C(Cl)C=C2)C=C1).Application In Synthesis of 4-Chloro-4′-ethynyl-1,1′-biphenyl. Through the article, more information about this compound (cas:57399-11-8) is conveyed.
This article focuses on the dehydration of α-hydroxy-tetrazoles, leading to tetraazafulvenes and then to vinylic carbenes that rearrange into ethynyl moieties through the Fritsch-Buttenberg-Wiechell rearrangement. Each step of this sequence was scrutinized, either by examination of the substrate and/or dehydrating agent scope, or through AM1 calculations, to understand the limiting step of this process. This underrated transformation appears to be a viable alternative to existing methods used for transforming aldehydes into alkynes.
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Reference:
Tetrahydroisoquinoline – Wikipedia,
1,2,3,4-Tetrahydroisoquinoline | C9H11N – PubChem