Some general characteristic properties of substituted cyclopentadienes

Миронов, В. А.; Sobolev, E. V.; Elizarova, A. N.

doi:10.1016/0040-4020(63)85008-5

Cited by 184 publications

(41 citation statements)

References 17 publications

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“…Thus, the major component in the mixture of 1 and 2 is isomer 2. Methylcyclopentadiene also contains more 2-than 1-isomer at equilibrium but the ratio is only 1.20: 1 (2,4). Since this ratio is opposite in sense to that expected from a hyperconjugative effect of the methyl group (4), and since the effect of replacing the methyl group with the larger triphenylmethyl group is to increase the fraction of 2-substituted diene in the equilibrium mixture, we suggest that the reason for the predominance of 2-alkyl cyclopentadienes over the 1-isomers has to do with greater steric hindra~ice in the latter.…”

Section: Isomers Of Triplzenylnzethylcyclopentadienementioning

confidence: 99%

“…A diradical representation is also useful for rationalizing the inefficient di-nmethane rearrangement of 2, for which an unconjugated. as opposed to an allylic, radical site develops along the reaction coordinate [2].…”

Section: Photochemistrymentioning

confidence: 99%

“…First, monosubstituted cyclopentadienes are interconverted by thermal [1,5]-sigmatropic hydrogen migration and are obtained as mixtures of isomers (1)(2)(3)(4)(5)(6), any one or all of which could be photolabile. Second, all three possible isomers have the endocyclic di-n-methane system of cyclopentadiene itself but, in the cases of 1-and 2-triphenylmethylcyclopentadienes, P and 2, respectively, there is an additional di-n-methane system consisting of a double bond of the diene moiety and a phenyl group.…”

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Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene

Weigl¹,

Warkentin²

1977

Can. J. Chem.

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Triphenylmethylcyclopentadiene exists as a mixture of isomers, the minor and major components of which are shown to be 1-triphenylmethylcyclopentadiene (1) and 2-triphenylmethyl-cyclopentadiene (2), respectively.Direct irradiation of a mixture of 1 and 2 led to formation of 5,6,6,-triphenylbicyclo[3.1.0]hex-2-ene (3) via rearrangement of 1. Acetophenone-sensitized irradiation of the same mixture gave 3 as well as a two component mixture of photodimers of 1 and/or 2. Results are interpreted in terms of the di-π-methane rearrangement mechanism.

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Section: Isomers Of Triplzenylnzethylcyclopentadienementioning

confidence: 99%

Section: Photochemistrymentioning

confidence: 99%

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confidence: 99%

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Photoisomerization of 1-triphenylmethylcyclopentadiene. Di-π-methane rearrangement to 5,6,6-triphenylbicyclo[3.1.0]hex-2-ene

Weigl¹,

Warkentin²

1977

Can. J. Chem.

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“…tetramethyl-4-aza-tricyclo[5.2.1.0 2,6 ]dec-8-ene-3,5-dione, hydrazine hydrate Various imide derivatives of 1,7,8,9-tetramethyl-4-aza-tricyclo[5.2.1.0 2,6 ]dec-8-ene-3,5-dione (2) have been reported and shown to exhibit an anxiolytic activities [1].…”

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confidence: 99%

“…]dec-8-ene-3,5-dione (1). The synthesis of (1) was performed from 1,2,3,4-tetramethyl-1,3-cyclopentadiene and furan-2,5-dione according to the method described previously [2]. …”

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confidence: 99%