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α‐Hydroxy‐Tetrazoles as Latent Ethynyl Moieties: A Mechanistic Investigation
Author(s) -
Quinodoz Pierre,
Wright Karen,
Drouillat Bruno,
Kletskii Mikhail E.,
Burov Oleg N.,
Lisovin Anton. V.,
Couty François
Publication year - 2019
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800143
Subject(s) - chemistry , scope (computer science) , sequence (biology) , limiting , combinatorial chemistry , transformation (genetics) , substrate (aquarium) , dehydration , stereochemistry , programming language , biochemistry , mechanical engineering , oceanography , computer science , engineering , gene , geology
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, in order 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.