Quinodoz, Pierre; Wright, Karen; Drouillat, Bruno; Kletskii, Mikhail E.; Burov, Oleg N.; Lisovin, Anton. V.; Couty, Francois published the article 《α-Hydroxy-Tetrazoles as Latent Ethynyl Moieties: A Mechanistic Investigation》. Keywords: hydroxytetrazole dehydration Fritsch Buttenberg Wiechell; alkyne preparation.They researched the compound: 4-Chloro-4′-ethynyl-1,1′-biphenyl( cas:57399-11-8 ).Application In Synthesis of 4-Chloro-4′-ethynyl-1,1′-biphenyl. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:57399-11-8) here.
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