[12]Annulynes from 1,5‐Hexadiyne and Potassium tert‐Butoxide? Franz Sondheimer’s Hexadienynes!

2009/12/10 by Manfred Christl, Henning Hopf · 1 citation
Chemistry · #Cyclization and Aryne Chemistry #Asymmetric Synthesis and Catalysis #Chemical synthesis and alkaloids

paper · doi:10.1002/anie.200901741

openalex publication_date 2009/12/10 · openalex created_date 2016/06/24 · openalex updated_date 2026/07/29

Abstract

Obscure mechanism: [12]Annulyne 1 and three of its isomers were reported in two recent publications as products from the reaction of potassium tert-butoxide (KOtBu) with 1,5-hexadiyne (2), although a plausible mechanism was not proposed. A careful examination of the NMR spectra has now proven that only the two possible 1,3-hexadien-5-ynes (3) were produced. This result had already been obtained by Sondheimer et al. in 1961.

Citations

• [12]Annulynes
• The Isomers of [12]Annulyne and their Reactive Relationships to Heptalene and Biphenyl

Cited by

• Annulyne [wikipedia]

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