A Novel Method for the Preparation of Bicyclooctane Systems<sup>1</sup>

Morita, Kenichi; Nishimura, Michio; Suzuki, Zennosuke

doi:10.1021/jo01013a057

Cited by 9 publications

(3 citation statements)

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“…Material in the 42-cm peak was collected from the gas chromatographic column by condensation into a glass capillary tube. Its infrared and nmr spectra [(CDCI3) 2.80, 2.86 (10 H, phenyl groups), 7.08-7.70 (multiplet, 2.9 H, protons a to phenyl group), 7.87-8.36 (multiplet, 2.0 H, OIL), 8.70 and 8.81 (doublet, 3.1 II, CH3)] were identical with those of authentic 1,3-diphenylbutane.15 Retention times of the two samples on gas chromatography were also identical.…”

Section: (1956)mentioning

confidence: 99%

1,2-Diphenylcyclobutene

Dodson¹,

Zielske²

1967

J. Org. Chem.

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Section: (1956)mentioning

confidence: 99%

1,2-Diphenylcyclobutene

Dodson¹,

Zielske²

1967

J. Org. Chem.

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“…C 6 compounds: 2-hexanone (11,101), 3,3-dimethyl-2-butanone (16,59,220), 6-formyloxyhexanal (4, 5), 2-methylcyclopentanone (5), cyclohexanone (12,151,178,190,215,248), 2-methyl-l-penten-3-one (8) (64,67,108,160,225), m-aminobenzaldehyde (42), m-and /?-nitrobenzaldehyde (108), /?-chlorobenzaldehyde (108), ο-, m-, and /7-hydroxybenzaldehyde (34,218), ο-, πι-, and /7-methoxybenzalde-hyde (67,108,151,160) (108,160,225), acetophenone (9,59,65,67,100,107,190,220), /7-bromoacetophenone (755), a-bromoacetophenone (159), a-chloroacetophenone (159), and 3-hydroxy-2-methyl-5-phosphoryloxymethyl-4pyridinecarboxaldehyde (155a). (207), and butyrophenone (59). C n compounds: 6-formyl-2,2,6-trimethylcycloheptanone (acetal) (243), and 2,2,6-trimethylcyclohexylideneacetaldehyde (149).…”

Section: T a B L E Ii Equilibrium Constants For Conversion Of Ketonesmentioning

confidence: 99%

“…(35)] (8,58,94,114,207,244), as well as the expected unsaturated ketals (116). The trialkoxy compound is probably formed by reaction of the conjugate acid of the ketone with the alcohol to form an alkoxyvinyl alcohol, followed by tautomerization to the alkoxy ketone, which then undergoes ketalization in the usual manner.…”

Section: T a B L E Ii Equilibrium Constants For Conversion Of Ketonesmentioning

confidence: 99%

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

1970

Carboxylic Ortho Acid Derivatives - Preparation and Synthetic Applications

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In this chapter are considered reactions of trialkyl orthocarboxylates and tetraalkyl orthocarbonates which result in the formation of new carbonoxygen or carbon-halogen bonds. In most of these reactions the ortho ester (or an alkoxycarbonium ion derived from it) functions as an alkylating agent.Many of these reactions are useful synthetic tools. These include formation and hydrolysis of cyclic ortho ester derivatives of diols and triols (which serve to protect the hydroxyl groups of the polyols, and provide means for their mild monoacylation), alkylation of phenols, enols and acids (to form ethers and esters), and conversion of carbonyl compounds to acetals and ketals. Other reactions, such as the alkylation of halogens by ortho esters, are of only limited synthetic utility, while still others, such as the acidcatalyzed hydrolyses of ortho esters, are of interest primarily because of the light they shed on the mechanisms of reactions of ortho esters with nucleophilic reagents.

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Bicyclische Verbindungen, XVIII^1,2) Solvolytische und reduktive Umlagerung von Bicyclo[2.2.2]‐octyltosylaten

Kraus

Chassin

et al. 1970

Justus Liebigs Ann. Chem.

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wlhrend das Chlortosylat l e (X = Cl) unter den gleichen Bedingungen sowohl die tertiaren Alkohole 4e und 5 e (X = CI) als auch die ungesattigten Produkte 7 e (X = C1) und 8 e (X = CI) liefert. Dieses unterschiedliche Verhalten wird auf induktive und Feldeffekte der Substituenten amBriickenkopf zuriickgefiihrt. DieReduktion vonl a-emit LiAlH4fuhrt ebenfalls weit iiberwiegend zu den ungesattigten Umlagerungsprodukten 7 und 8; die Zusammensetzung der Reaktionsprodukte hangt jedoch bei der Reduktion starker von der Natur der Substituenten an C-4 ab als bei den Solvolysen. Aus den Ergebnissen folgt, da8 auch die reduktiven Umlagerungen iiber Carbonium-Ionen als Zwischenstufen verlaufen. Bicyclic Compounds, XVIII1.2). Solvolytic and Reductive Rearrangements of Bicyclo[2,2,2]-octyl TosylatesThe solvolyses of 4-substituted l-methyl-bicyclo[2,2,2]octyl-(2) tosylates 1 a (X = H), 1 b (X = OH), l c (X = OAc), I d (X = OCH3), and l e (X = CI) lead to derivatives of bicyclo-[3,2,l]octane in quantitative rearrangement. From 1 a (X = H) the tertiary 2-methyl-bicyclo-[3,2,l]octan-2-ols (4a and 5a: X = H) are obtained; but from l b , l c , and I d the 2-methyl-bicyclo[3,2,l]oct-2-enes (7b: X = OH, 7 c : X = OAc, 7 d : X = OCH3) are mainly formed along with little amounts of rnethylenebicyclooctanes 8 b (X = OH), 8c (X = OAc), and 8 6 (X = OCH3). On the other hand, chlorotosylate l e (X = CI) during solvolysis under similar conditions yields a mixture of tertiary alcohols 4 and 5 (X = CI), and the unsaturated compounds 7 e (X = CI) and 8e (X = CI). This difference in behaviour is explained by *) Meinem hochverehrten Lehrer, Herrn Prof. Dr., Dr. h. c. mult. Walter Hiickel, zum 75.

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A Novel Method for the Preparation of Bicyclooctane Systems¹

Cited by 9 publications

References 0 publications

1,2-Diphenylcyclobutene

1,2-Diphenylcyclobutene

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

Bicyclische Verbindungen, XVIII^1,2) Solvolytische und reduktive Umlagerung von Bicyclo[2.2.2]‐octyltosylaten

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A Novel Method for the Preparation of Bicyclooctane Systems1

Cited by 9 publications

References 0 publications

1,2-Diphenylcyclobutene

1,2-Diphenylcyclobutene

Reactions of Ortho Esters Which Result in Carbon-Oxygen and Carbon-Halogen Bond Formation

Bicyclische Verbindungen, XVIII1,2) Solvolytische und reduktive Umlagerung von Bicyclo[2.2.2]‐octyltosylaten

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A Novel Method for the Preparation of Bicyclooctane Systems¹

Bicyclische Verbindungen, XVIII^1,2) Solvolytische und reduktive Umlagerung von Bicyclo[2.2.2]‐octyltosylaten