The Isomerization of Cyclooctadienes to cis-Bicyclo[3.3.0]oct-2-ene

Stapp, Paul R.; Kleinschmidt, Roger F.

doi:10.1021/jo01020a027

Cited by 37 publications

(4 citation statements)

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“…The bicyclo product was identified by ir, nmr, mass spectrometry, and refractive index. Its properties agreed with those of an authentic sample (Stapp and Kleinschmidt, 1956).…”

Section: Methodssupporting

confidence: 72%

Selective Transition Metal Catalysts Complexed with Triphenyl Phosphine

Itatani¹,

Bailar²

1972

Product R&D

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Linear, cyclic, terminal, and sterlcally hindered diolefins were hydrogenated with Nil2(4>3P)2, PtCI2{03P)2 + SnCI2, PdCI2(03P)2 + SnCI2, and Pd(CN)2(4>3P)2 as catalysts. Rapid migration of Ihe double bonds formed conjugated dienes subsequently hydrogenated to monoenes. The substituted monoolefins formed were not further hydrogenated, except for the terminal olefins. Differences in the mode of hydrogen addition to a 146 Ind. Eng. Chem.

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“…The bicyclo product was identified by ir, nmr, mass spectrometry, and refractive index. Its properties agreed with those of an authentic sample (Stapp and Kleinschmidt, 1956).…”

Section: Methodssupporting

confidence: 72%

Selective Transition Metal Catalysts Complexed with Triphenyl Phosphine

Itatani¹,

Bailar²

1972

Product R&D

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“…[58] Base mediated routes from 1,5-or 1,3-cyclooctadiene to 3 are available as well. [65] Since one could speculate pathways to ring non-contracted olefins like 1,3-cyclooctadiene and 1,2-cyclooctadiene (an allene) via C-H insertions to 7 (and G rel values for cyclooctyne, 1,3-cyclooctadiene and 1,2-cyclooctadiene are 35.4, 13.6, and 29.8 kcal/mol), we tested the chemistry of 1,3-or 1,5-cyclooctadiene using either gold catalyst or strong acid (100 or 120°C in CHCl 3 ). As evident from the data presented in Supporting Information, either no products of 2 and Figure 4).…”

Section: Resultsmentioning

confidence: 99%

Gold‐Mediated Isomerization of Cyclooctyne to Ring Fused Olefinic Bicycles

et al. 2016

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“…Bicyclo[5.3.0]-1(7)-decene (52) was formed on isomerization of bicyclo [5.3.0]-l(2)decene (21) with p-toluenesulfonic acid, and was isolated from the mixture of isomers by chromatography with cyclohexane on silica gel impregnated with 10% of silver nitrate. cis-Bicyclo[3.3.0] octane (42) was obtained upon hydrogenation of cis-bicyclo[3.3.0]-2-octene [45]. A mixture of ca.…”

mentioning

confidence: 99%