Bicyclo[2.2.0]hex-1(4)-ene

Wiberg, Kenneth B.; Matturro, Michael G.; Okarma, Paul J.; Jason, Mark E.; Dailey, William P.; Burgmaier, George J.; Bailey, William F.; Warner, Philip

doi:10.1016/s0040-4020(01)87609-2

Cited by 76 publications

(32 citation statements)

References 53 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Interestingly, this subset includes C−C bonds that have been classified as “exotic” bonds previously, and a large number of studies have been conducted in the last decades to elucidate the detailed nature of these bonds. The members are the naked “formally” triple C−C bond in ortho ‐benzyne ( 73 ), the central single C−C bond in the highly strained bicyclo‐1,1,0‐butane ( 77 ), the strongly deformed central double bond in the strained bicyclo‐2,2,0‐hex‐1,4‐ene ( 81 ), and finally the central inverted C−C bond in 988 . The computed % ρ (%▿ 2 ρ ) are 34, 12, and 35 (72, 121, and 82) for 73 , 77 , and 81 , respectively.…”

Section: Resultsmentioning

confidence: 99%

Tracing the Fingerprint of Chemical Bonds within the Electron Densities of Hydrocarbons: A Comparative Analysis of the Optimized and the Promolecule Densities

2016

View full text Add to dashboard Cite

The equivalence of the molecular graphs emerging from the comparative analysis of the optimized and the promolecule electron densities in two hundred and twenty five unsubstituted hydrocarbons was recently demonstrated [Keyvani et al. Chem. Eur. J. 2016, 22, 5003]. Thus, the molecular graph of an optimized molecular electron density is not shaped by the formation of the C-H and C-C bonds. In the present study, to trace the fingerprint of the C-H and C-C bonds in the electron densities of the same set of hydrocarbons, the amount of electron density and its Laplacian at the (3, -1) critical points associated with these bonds are derived from both optimized and promolecule densities, and compared in a newly proposed comparative analysis. The analysis not only conforms to the qualitative picture of the electron density build up between two atoms upon formation of a bond in between, but also quantifies the resulting accumulation of the electron density at the (3, -1) critical points. The comparative analysis also reveals a unified mode of density accumulation in the case of 2318 studied C-H bonds, but various modes of density accumulation are observed in the case of 1509 studied C-C bonds and they are classified into four groups. The four emerging groups do not always conform to the traditional classification based on the bond orders. Furthermore, four C-C bonds described as exotic bonds in previous studies, for example the inverted C-C bond in 1,1,1-propellane, are naturally distinguished from the analysis.

show abstract

Section: Resultsmentioning

confidence: 99%

Tracing the Fingerprint of Chemical Bonds within the Electron Densities of Hydrocarbons: A Comparative Analysis of the Optimized and the Promolecule Densities

2016

View full text Add to dashboard Cite

show abstract

“…The synthesis of a highly strained didehydro [2]ladderane has been accomplished using a Favorskii ring contraction reaction of a dichlorobicycloheptanone as shown at the top of Scheme (6) [35]. The bromochloro- [2]ladderane precursor to the didehydro [2]-ladderane could also be reduced to the parent [2]-ladderane.…”

Section: Target Oriented Multistep Synthesesmentioning

confidence: 99%

They Came From the Deep: Syntheses, Applications, and Biology of Ladderanes

Nouri¹,

Tantillo²

2006

COC

View full text Add to dashboard Cite

Ladderanes are hydrocarbons consisting of two or more fused cyclobutane rings. These molecules and their derivatives are of fundamental interest to physical organic chemists due to their strain and electronic properties. Recently, the astonishing discovery that some bacterial lipids contain ladderane substructures has revitalized interest in this class of molecules. This review describes the synthesis, reactivity, applications, and biology of ladderanes.

show abstract

“…41 The dramatic effects of perfluorination can be seen in the chemistry of perfluorobicyclo[2.2.0]hex-1(4)-ene (25). Unlike its hydrocarbon parent, which is very labile towards dimerization and polymerization, 45 25 is thermally more robust, and is an extremely reactive dienophile, adding across aromatic molecules including naphthalene, durene and even benzene (Scheme 10). 46 2-Fluoroacrylic ester 26a, incorporating the 8-phenylmenthol chiral auxiliary, undergoes an asymmetric Diels-Alder reaction with cyclopentadiene in the presence of various Lewis acids (Scheme 11A).…”

Section: [4d2] Cycloadditionsmentioning

confidence: 99%