Stereochemical specificities of carbonyl compounds of the Δ3-cyclohexene series

Kugatova-Shemyakina, G. P.; Ovchinnikov, Yu.A.

doi:10.1016/s0040-4020(01)92723-1

Cited by 13 publications

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“…In benzene (150 ml) in the presence of 0.15 mole of anhydrous aluminum chloride. 6 Room-temperature (co. 25°) reaction in a sealed tube, and 120°reactions in a stainless steel autoclave.…”

Section: Resultsmentioning

confidence: 99%

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Aluminum chloride catalyzed diene condensation. III. Reaction of trans-piperylene with methyl acrylate

Inukai¹,

Kojima²

1967

J. Org. Chem.

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Section: Resultsmentioning

confidence: 99%

“…d By glpc analysis of the aromatization products. 6 By glpc analysis of the cyclohexenecarboxylates. ' By glpc analysis of the cyclohexanecarboxylates.…”

Section: Resultsmentioning

confidence: 99%

Aluminum chloride catalyzed diene condensation. III. Reaction of trans-piperylene with methyl acrylate

Inukai¹,

Kojima²

1967

J. Org. Chem.

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“…This result probably reflects the fact that the 1,4-benzodioxan system has more cyclohexane-type character than cyclohexene. Russian workers [9] have also postulated that certain cyclohexene aldehydes and ketols are formed with the substituent in the axial position but this may be due to specific interactions with the double bond. These two reports appear to be the only indications of axial substituents, the majority assuming that monosubstitution follows the cyclohexane pattern.…”

Section: Discussionmentioning

confidence: 99%

Calculations of chemical shifts

Feeney

Sutcliffe²,

Walker³

1966

Molecular Physics

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The application of electric field theory to a study of fluorinated cyclohexene molecules [1] is continued with the investigation of 1,2,4-trichloroheptafluorocyclohexene. This compound is considered to exist as a fixed conformer at room temperature and the calculations have been performed with the ring chlorine atom occupying axial and equatorial positions in turn. Studies at higher temperatures have enabled the other conformer to be investigated and the results show that the ring chlorine atom probably occupies an axial position in the predominant conformer. This conclusion is the opposite of that normally proposed for cyclohexenes which have previously been assumed to follow the cyclohexane pattern.

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Über die Chemie des Vitamins E. 3. Mitteilung. Die Totalsynthese von (2R, 4′R, 8′R)‐ und (2S, 4′R, 8′R)‐α‐Tocopherol

Mayer

Schudel

Rüegg

et al. 1963

Helvetica Chimica Acta

101

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(2R, 4′R, 8′R)‐ and (2S, 4′R, 8′R)‐α‐tocopherol have been synthesized by WITTIG reaction of the two enantiomeric S‐(+)‐ and R‐(−)‐6‐acetoxy‐Z‐formyl‐2,5,7, 8‐tetramethyl‐chromans (I) with (3R, 7R)‐hexahydrofarnesyl‐triphenylphosphonium bromide (II), followed by hydrogenation and hydrolysis. (2R, 4′R, 8′R)‐α‐tocopherol proved to be identical in every respect with natural so called d‐α‐tocopherol. Resolution of the chroman component was achieved via the diastereomeric quinine salts of 2‐carboxyethynyl‐6‐hydroxy‐2,5,7,8‐ tetramethyl‐chroman (XVIII). followed by transformation of the enantiomers into S‐(+)‐ and R‐(−)‐I, respectively.

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Stereochemical specificities of carbonyl compounds of the Δ3-cyclohexene series

Cited by 13 publications

References 0 publications

Aluminum chloride catalyzed diene condensation. III. Reaction of trans-piperylene with methyl acrylate

Aluminum chloride catalyzed diene condensation. III. Reaction of trans-piperylene with methyl acrylate

Calculations of chemical shifts

Über die Chemie des Vitamins E. 3. Mitteilung. Die Totalsynthese von (2R, 4′R, 8′R)‐ und (2S, 4′R, 8′R)‐α‐Tocopherol

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