Electronic structure of the tricyclo[2.1.0.02,5]pentane system. Photoelectron spectroscopic investigations of 1,5-dimethyl-3-exo-methylenetricyclo[2.1.0.02,5]pentane and 1,5-dimethyltricyclo[2.1.0.02,5]pentan-3-one

Abstract

Electronic Structure of the Tricyclo[2.1.0.02,5]pentane System.Photoelectron Spectroscopic Investigations of 1,5-Dimethy 1-3-exo -methylenetricyclo[2.1.0.02,5]pentane and 1,5-Dimethy ltricyclo[2.1.0.02,5] pentan-3-one

Bicyclo[1.1.1]pentanes, [n]Staffanes, [1.1.1]Propellanes, and Tricyclo[2.1.0.02,5]pentanes

“…It has been assigned to ionization out of a symmetric MO localized primarily on the carbon atoms of the bicyclo[1.1.0]butane fragment. The first IP of tricyclo[2.1.0.0 2,5 ]pentan-3-one ( 98 ) is 9.15 eV …”

“…Photoelectron spectrum of 3 has not been measured, but for 3-methylenetricyclo[2.1.0.0 2,5 ]pentane (103) the first IP is 8.54 eV. 147 It has been assigned to ionization out of a symmetric MO localized primarily on the carbon atoms of the bicyclo[1.1.0]butane fragment. The first IP of tricyclo[2.1.0.0 2,5 ]pentan-3-one (98) is 9.15 eV.…”

Exploration of C6H6 Potential Energy Surface: A Computational Effort to Unravel the Relative Stabilities and Synthetic Feasibility of New Benzene Isomers

“…In addition to the valence isomers of benzene, several other isomers, both cyclic and acyclic, exist and are interesting in their own right. − Exploration of the structural limitations in organic chemistry is an inspiring and challenging arena, which warrants a judicious combination of experiment and theory. Several experimental studies have been reported on the rearrangements of acyclic isomers of C 6 H 6 in generating other acyclic and cyclic isomeric structures. − Prominently, the rearrangement of 1,5-hexadiyne to other isomeric forms of C 6 H 6 has been the interest for more than three decades. − ,− Huntsman and Wristers have synthesized 3,4-dimethylenecyclobutene, a monocyclic isomer, in high yield from 1,5-hexadiyne by thermal cyclization at 350 °C, which was reported to occur via 1,2,4,5-hexatetraene .…”

Isomerizations of Bicyclo[2.1.0]pent-2-ene and Tricyclo[2.1.0.02,5]pentane into Cyclopenta-1,3-diene: A Computational Study by DFT and High-Level ab Initio Methods

“…There have been several experimental studies of the thermal rearrangements of tcp and its derivatives. − Unfortunately, no experimental reaction parameters are available for the ring opening of this molecule. We are not aware of any high-level computational investigation of the rearrangement process in tcp .…”