1430199-75-9Relevant academic research and scientific papers
(E,E)-1,2,3,4-tetracyclopropylbuta-1,3-diene: Synthesis and some of its properties
De Meijere, Armin,Redlich, Stefan,Kozhushkov, Sergei I.,Yufit, Dmitry S.,Magull, Joerg,Vidovic, Denis,Schill, Heiko,Menzel, Henning
, p. 6953 - 6958 (2013/02/25)
(E,E)-1,2,3,4-Tetracyclopropylbuta-1,3-diene (3) and (Z,Z)-1,4-diodo-1,2,3, 4-tetracyclopropylbuta-1,3-diene (4) were prepared from dicyclopropylacetylene via an intermediate 2,3,4,5-tetracyclopropyltitanacyclopentadiene (2) in 91 and 77 % yield, respectively. In the crystal, 3 adopts a conformation with an almost coplanar (I = 163°) 1,3-diene core, with the inner vinylcyclopropane units in an orthogonal and the outer vinylcyclopropane moieties in an s-trans orientation. This diene, like 2,3-cyclopropylbuta-1,3-diene (5), undergoes facile concerted [4+2] cycloadditions at 130 °C with dimethyl acetylenedicarboxylate as well as N-phenylmaleimide and at 0°C with N-phenyltriazolinedione. An X-ray crystal structure analysis of 2,3-dicyclopropylbuta-1,3-diene (5) also reveals a coplanar inner core with the vinylcyclopropane units in essentially orthogonal (Iav = 89.3°) orientation. Differential scanning calorimetry (DSC) measurements indicate that 3 undergoes significant internal reorganization on going from the liquid to the crystalline phase, and a gauche conformer of 3 may well be favored over the s-trans conformer in the liquid. Copyright
