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.
- ^ Georgian, Vlasios; Saltzman, Martin (1972). "Syntheses directed toward saturated "flat" carbon". Tetrahedron Letters. 13 (42): 4315–4317. doi:10.1016/S0040-4039(01)94304-7.
- ^ a b Nickon, Alex; Silversmith, Ernest F. (2013). Organic Chemistry: The Name Game: Modern Coined Terms and Their Origins. Elsevier. pp. 55–56. ISBN 9781483145235.