Enine

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Enine
( eponymous groups marked in blue )
Enin
General structure of
a conjugated enyne
(R 1 –R 4 org. Residues or H)
Butenine
Butenine (vinylacetylene)
simplest enyne
Gephyrotoxin
Gephyrotoxin - Simplified Formula
(Conjugated Enyne)
AMG-1
AMG-1 - simplified formula
(isolated enyne)

The enynes are a group of substances that contain a C = C double bond and a C≡C triple bond . The name is derived from the suffixes -en (from alkene ) and -in (from alkyne ).

The simplest representative of this group is butenine (vinylacetylene).

Classification

Depending on the position of the double and triple bond, a distinction is made between isolated and conjugated enynes. The enynes form a subgroup of the enynes .

Occurrence and use

Harlequin tree cutters ( Oophaga histrionica )

Enynes can be produced synthetically, but they also occur in nature. For example, gephyrotoxin is found in harlequin tree climbers .

Enynes are used in organic chemistry, for example in enyne metathesis for the production of 1,3- dienes . Furthermore, allenes can be prepared via enynes in a conjugate 1,6-addition .

See also

Commons : Enynes  - collection of images, videos and audio files
Commons : Enyne metathesis  - collection of images, videos and audio files

Individual evidence

  1. ↑ Marco Santarem, Corinne Vanucci-Bacqué & Gérard Lhommet: Formal Total Synthesis of (+) - Gephyrotoxin. In: The Journal of Organic Chemistry , Vol. 73 (16), pp. 6466-6469. doi : 10.1021 / jo801150e .
  2. ↑ Steven T. Diver & Anthony J. Giessert: Enyne Metathesis (Enyne Bond Reorganization). In: Chemical Reviews 2004, Vol. 104 (3), pp. 1317-1382. doi : 10.1021 / cr020009e .
  3. ↑ N. Krause, A. Gerold: Regio- and stereoselective syntheses with organocopper reagents. In: Angewandte Chemie 1997, Vol. 109 (3), pp. 194-213. doi : 10.1002 / anie.19971090304 .