1963
DOI: 10.1021/jo01040a055
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Bridged Polycyclic Compounds. XXI. The Ionic Chlorination of 9, 10-Dihydro-9, 10-ethenoanthracene1

Abstract: The ionic chlorination of 9,10-dihydro-9,10-ethenoanthracene was shown to yield exo-and endo-4-syn-8dichlorodibenzobicyclo[3.2.1 ]octadiene as the sole reaction products. The less stable of these isomers was the preponderant product. The structure proofs of these addition-rearrangement reaction products and some of their chemistry are discussed. Ionic chlorination of 9,10-dihydro-9,10-ethenoanthracene (I) in carbon tetrachloride gave two isomeric dichlorides, A and B, neither of which were cisor trans-11,12-di… Show more

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Cited by 13 publications
(7 citation statements)
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“…However, 1,3-diphenyl-1-propanol (7) gave up to 34% cylization product, 1-phenylindan, as well as the main product, a higher boiling one which we believe to be the result of intermolecular condensation reactions. 6 The ability of this secondary phenylalkanol to undergo cyclialkylation confirms the idea that a stable carbonium ion intermediate, in this case stabilized by a phenyl group, is required.…”
Section: Resultssupporting
confidence: 57%
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“…However, 1,3-diphenyl-1-propanol (7) gave up to 34% cylization product, 1-phenylindan, as well as the main product, a higher boiling one which we believe to be the result of intermolecular condensation reactions. 6 The ability of this secondary phenylalkanol to undergo cyclialkylation confirms the idea that a stable carbonium ion intermediate, in this case stabilized by a phenyl group, is required.…”
Section: Resultssupporting
confidence: 57%
“…Upon treatment with sulfuric acid at room temperature, the two tertiary alcohols, 2-methyl-4-phenyl-2butanol (4) and 2-methyl-5-phenyl-2-pentanol (5), gave 1,1-dimethylindan and 1,1-dimethyltetralin, respectively. The secondary alcohol, 5-phenyl-3-pentanol (6), gave 1-methyltetralin. These were the products reported by Roblin,Davidson,and Bogert.3 It should be noted that a hydrogen shift, converting one secondary carbonium ion to another, allows the formation of the tetralin in preference to the indan4 in the last case.…”
Section: Resultsmentioning
confidence: 99%
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“…Direct acid-mediated ring interconversion of bicyclo[2.2.2]octene ( 501 ) was found to give, depending on the reaction conditions, the bicyclooctanol 182 106 or the bicyclo[3.2.1]octene 502 , while performic acid oxidation furnished diol 503 in quantitative yield, a transformation also effective with dibenzobicyclo[2.2.2]octadiene . Similarly, the deamination of bicyclic amines, Hell−Volhard−Zelinsky bromination of bicyclo[2.2.2]octane-2-carboxylic acid, ionic chlorination, and also radical addition of HBr 292 to unsaturated [2.2.2] bridged precursor proceed with isomerization to the corresponding functionalized bicyclo[3.2.1]octane derivatives.
…”
Section: Rearrangement Of Polycyclic Intermediatesmentioning
confidence: 99%
“…Rearranged products have also been observed in the chlorination of dibenzobicyclo[2.2.2]octadiene (142), norbornene (1 36), and benzonorbornadiene (143). Rearranged products have also been observed in the chlorination of dibenzobicyclo[2.2.2]octadiene (142), norbornene (1 36), and benzonorbornadiene (143).…”
Section: R C Faheymentioning
confidence: 91%