Carbon Rich Compounds II, Macrocyclic Oligoacetylenes and by Armin de Meijere

By Armin de Meijere

The definition of Carbon wealthy Compounds utilized during this as within the earlier quantity (TCC quantity 196) of this sequence at the similar common subject contains carbon skeletons with a carbon to hydrogen ratio of 1:(kleiner gleich 1), which eventually implies all-carbon compounds (i.e. carbon allotropes). the present quantity covers glossy tools for the coupling - typically steel catalyzed - of subsystems inclusive of double bonds, cyclopropyl teams, arenes, and metal-complexed pi-systems with acetylene and diacetylene devices. The ensuing buildings diversity from macrocycles, together with people with every kind of linkers among the acetylene and diacetylene devices, to accomplishing polymers and light-emitting fabrics. anyplace acceptable, chemical modifications of those fascinating compounds and fabrics are mentioned as well.

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Extra info for Carbon Rich Compounds II, Macrocyclic Oligoacetylenes and Other Linearly Conjugated Systems

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2 The Transition-Metal Route to Cyclocarbons Although the preparation of bulk quantities of free cyclo-C18 remains elusive, a transition metal complex could be prepared and characterized by X-ray crystallography [41, 42]. Complexation of an alkyne with [Co2(CO)8] leads to a reduction of the C∫C–C angles in the formed (µ-acetylene)dicobalt hexacarbonyl complex to values around 140° [43, 44]. Therefore, dicobalt hexacarbonyl fragments have been used as protecting groups to allow geometrically disfavored cyclization reactions by bending an alkyne moiety [45, 46].

A distinct bathochromic shift is observed on going from 1,4-dicyclopropylbutadiyne via 165–168 to 171; and, more interestingly, this absorption splits into two bands for macrocycles 165–168 and 171, but with different magnitudes [37]. This must be due to the expected increased homoconjugative interaction between ethynyl units in the “blown-up” [n]rotanes, as corresponding effects are not observed in the UV spectra of the analogous permethylated macrocycles of types 3 and 84 [4, 6, 7]. The UV spectra of expanded [n]rotanes 127 and 128, however, were similar to those of the monomeric diyne 118 except for the increased molar extinction coefficient.

60 . . . . . . . 62 . . . . . . . 64 Topics in Current Chemistry, Vol. 201 © Springer-Verlag Berlin Heidelberg 1999 44 F. Diederich · L. 3 Donor-Acceptor Substituted Tetraethynylethenes . . . . . 1 Preparation, Physical Properties, and Photochemical transÆcis Isomerization . . . . . . . . . . . . 2 Structure-Property Relationships in Nonlinear Optical Tetraethynylethenes . . . . . . . . . . . . . . 72 4 Conclusions . . . . . . . . . . .

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