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Cumulene
A cumulene is a hydrocarbon with three or more ''cumulative'' (consecutive) double bonds. A member of this compound class is butatriene (which is also called simply ''cumulene''), H2C=C=C=CH2.〔IUPAC Gold Book (IUPACs definition of cumulenes )〕 Unlike most alkanes and alkenes, cumulenes tend to be rigid, which makes them appealing for molecular nanotechnology. Polyynes are another kind of rigid carbon chains. Cumulenes are found in regions of space where hydrogen is rare (see astrochemistry). Cumulenes containing heteroatoms are called heterocumulenes. Examples include carbon suboxide and sulfur dioxide and their imido analogues, sulfur diimides (S(NR)2) and sulfinylamines (RNSO).
==Synthesis==
The first reported synthesis of a butatriene is that of tetraphenylbutatriene in 1921.〔Brand, K. (1921), ''Über Untersuchungen in der Tetraarylbutan-Reihe und über das 1.1 4.4-Tetraphenyl-butatrien''. (4. Mitteilung über die Reduktion organischer Halogen-verbindungen.). Berichte der deutschen chemischen Gesellschaft (A and B Series), 54: 1987–2006. 〕 The most common synthetic method for butatriene synthesis is based on reductive coupling of a geminal dihalovinylidene.〔''Synthesis of the Butatriene C4 Function: Methodology and Applications'' Léo Leroyer, Valérie Maraval, and Remi Chauvin Chemical Reviews Article ASAP 〕 Tetraphenylbutatriene was reported synthesized in 1977 by homocoupling of ''2,2-diphenyl-1,1,1-tribromoethane'' with elemental copper in dimethylformamide.〔''Convenient Preparation of Tetraarylbutatrienes'' TAKEHISA KUNIEDA and TAKEO TAKIZAWA CHEMICAL & PHARMACEUTICAL BULLETIN Vol.25 , No.7(1977)pp.1809-1810 〕
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