Chemical compound with four carbon rings sharing a single carbon atom
Fenestranes, from left to right: generic fenestrane, [4.4.4.4]fenestrane with carbon atoms shown and [5.5.5.5]fenestrane
A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused carbocycles.[1] They can be regarded as spiro compounds twice over. Because of their inherent strain and instability, fenestranes are of theoretical interest to chemists. The name—proposed in 1972 by Vlasios Georgian and Martin Saltzman[2]—is derived from the Latin word for window, fenestra. Georgian had intended that "fenestrane" solely referred to [4.4.4.4]fenestrane, whose skeletal structure looks like windows, and Kenneth B. Wiberg called that specific structure "windowpane".[3] The term fenestrane has since become generalized to refer to the whole class of molecules that have various other ring-sizes. Georgian recommended rosettane for the class, based on the structural appearance as a rosette of flowers.[3]
^Venepalli, Bhaskar Rao; Agosta, William C. (1987). "Fenestranes and the flattening of tetrahedral carbon". Chem. Rev.87 (2): 399–410. doi:10.1021/cr00078a007.
^ abNickon, Alex; Silversmith, Ernest F. (2013). Organic Chemistry: The Name Game: Modern Coined Terms and Their Origins. Elsevier. pp. 55–56. ISBN 9781483145235.
A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused carbocycles...
2003 song by Opeth from Damnation Windowpane, the structure of [4,4,4,4]Fenestrane Windowpane, a piece of gelatin containing LSD Windowpane coconut or Beccariophoenix...
1]propellane; or more generally the paddlanes, and pyramidane ([3.3.3.3]fenestrane). Such molecules are typically strained, resulting in increased reactivity...
production of nitrogen and water from nitrite ions and ammonia. Some related fenestranes are also found in nature.[citation needed] Cyclobutane photo dimers (CPD)...
below. Other examples include barrelene (shaped like a barrel),: 58 fenestrane (having a window-pane motif),: 55 ladderane (a ladder shape), olympiadane...
producing graphane. A square tiling (which would resemble an infinitely large fenestrane) would suffer from the same problem as octahedrane, and the triangular...
Laurenene is a diterpene natural product with an unusual [5.5.5.7]fenestrane structure. It was first discovered in extracts from the New Zealand tree species...
joined by four chains". Tetrahedron Letters. 14 (7): 507. doi:10.1016/S0040-4039(01)95684-9. Propellane Fenestrane Inverted tetrahedral geometry v t e...
A Sesquiterpenoid-Derived Metabolite Containing a Novel Dioxa[5,5,5,6]fenestrane Ring System from a Fungicolous Isolate of Penicillium griseofulvum". Organic...
ring. Hopf, Henning; Joel F. Liebman; H. Mark Perks (2009). "Cubanes, fenestranes, ladderanes, prismanes, staffanes and other oligocyclobutanoids". PATAI's...
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