Stereochemistry of some derivatives of phenylcyclohexane

Berti, G.; Bottari, F.; Macchia, B.; Macchia, Franco

doi:10.1016/0040-4020(66)80118-7

Cited by 24 publications

(23 citation statements)

References 15 publications

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“…Reacting styrene oxide with acetic acid a t room temperature gave mixtures of the two monoacetates 3a and 4a (Table I), in accordance with that found earlier by Berti et al (1) and Cohen et al (6), and not 2-acetoxy-1-phenylethanol (10). At about +3' only 2-acetoxy-2-phenylethanol l a was obtained, the first time this has been demonstrated and vindicating suggestions by others (1,6).…”

Section: Resultssupporting

confidence: 79%

“…At about +3' only 2-acetoxy-2-phenylethanol l a was obtained, the first time this has been demonstrated and vindicating suggestions by others (1,6).…”

Section: Resultsmentioning

confidence: 63%

“…Synthetic (1,2) and kinetic (3) studies of the ring-opening reactions of styrene oxide have gone a long way towards elucidation of the mechanism. The difficulty in studies of this type has been the qualitative and quantitative analysis of the often complex product mixtures obtained (4,5).…”

Section: Introductionmentioning

confidence: 99%

“…Isomer mixtures are frequently obtained on the opening of unsymmetrical epoxides (e.g. 1,6) and the first-formed isomer mixture with carboxylic acids may undergo ready acyl migration with heat or even mildly acidic or alkaline conditions, as seen with glyceryl part esters (7). Concomitant epoxide rearrangements in the presence of acid or base give by-products which complicate ring-opened product recovery and analysis (8,9), and low polyrner oils from condensation of two or three units of original epoxide (5, 10) also contribute to the difficulties.…”

Section: Introductionmentioning

confidence: 99%

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Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Hocking¹

1974

Can. J. Chem.

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Mixtures of ring-opened and other products of reactions of acetic or benzoic acids, or ethanol, or phenol with styrene oxide under various conditions can be qualitatively and quantitatively analyzed without isolation of the components by the use of n.m.r. This method, in the case of the ester products, avoids confusing the initial ring-opening result with the results observed after subsequent acyl migrations which readily occur in this type of system.

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Section: Resultssupporting

confidence: 79%

“…At about +3' only 2-acetoxy-2-phenylethanol l a was obtained, the first time this has been demonstrated and vindicating suggestions by others (1,6).…”

Section: Resultsmentioning

confidence: 63%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Hocking¹

1974

Can. J. Chem.

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“…C14H3202Si; (288, 6) Calc. C 58,25 H 11,20 Found C 58,36 H 11,02 Because the monoester resulting from p-toluenesulfonic acid and cyclohexyl-l,2-ethanediol (mixture 3/4) could not be isolated in crystalline form, 9,6 g of yellow viscous liquid were reduced by l o g of lithium aluminium hydride in 200ml of tetrahydrofuran.…”

Section: Synthesis Of S-( + )-Cyclohexjdepoxvethane (1)mentioning

confidence: 99%

Stereochemistry of copolymerization of optically active cyclohexylepoxyethane with carbon dioxide

1976

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The stereochemistry of alternating copolymerization ofcarbon dioxide with S-( + )-cyclohexylepoxyethane (1) using a diethylzinc/water system as catalyst was investigated. The optically active copolymer, poly[(oxycarbonyloxy)-1 -cyclohexylethylene], was hydrolyzed and the epoxide was transformed into the form 1,2-bis(trimethylsilyloxy)-I -cyclohexylethane (2). From the determination of optical activity of this ether, it is concluded that the ring opening of 1 in the copolymerization takes place predominantly at the methylene-oxygen linkage. ZUSAMMENFASSUNG:Die Stereochemie der alternierenden Copolymerisation von S-( + )-Cyclohexylepoxyathan (1) mit COz, initiiert durch ein Diathylzink/Wasser-System, wurde untersucht. Das erhaltene optisch aktive Polycarbonat, Poly[(oxycarbonyloxy)-1 -cyclohexylathylen], wurde hydrolysiert und der Epoxidbaustein in Form des 1,2-bis(trimethylsilyloxy)-1 -cyclehexylathans (2) isoliert. Aus der optischen Aktivitat dieser Verbindung wird geschlossen, SaB die Ringoffnung des Epoxidringes bei der Copolymerisation vorwiegend an der Methylen-Sauerstoff-Bindung erfolgt.

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Stereochemistry of the copolymerization of carbon dioxide with optically active phenylepoxyethane

1975

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The stereochemistry of the copolymerization of optically active phenylepoxyethane (5) with carbon dioxide using a diethylzinc/water system as catalyst was investigated. The optically active copolymer, poly(oxycarbonyloxy-2-phenylethylene) (l), was hydrolyzed and the oxy-2-phenylethylene unit was isolated in the form of 1,2-bis(trimethylsilyIoxy)-1-phenylethane (3). The determination of the optical activity of this ether led to the conclusion that the ring opening of 5 takes place predominantly at the methineoxygen linkage accompanying an inversion in the copolymerization. This fact is in sharp contrast with the stereochemistry of the copolymerization of carbon dioxide with 1.2-epoxypropane in which the ring opening takes place at the methylene-oxygen linkage. ZUSAMMENFASSUNG:Die Stereochemie der Copolymerisation von optisch aktivem Phenylepoxyzthan (5) mit Kohlendioxid unter Verwendung des Systems Di%thylzink/Wasser als Katalysator, wurde untersucht. Das optisch aktive Copolymere, Poly(oxycarbonylo~y-2-phenylathylen) (l), wurde hydrolysiert, wobei die Oxy-2-phenylathylen-Einheit als 1.2-Bis(trimethylsilyIoxy)-1-phenylathan (3) isoliert wurde. Aus der Bestimmung der optischen Aktivitat dieses Athers ergab sich, dalj die Ringoffnung von 5 wahrend der Copolymerisation bevorzugt an der Methin-Sauerstoff-Bindung stattfindet und von einer Inversion begleitet ist. Diese Tatsache befindet sich in scharfem Gegensatz zur Stereochemie der Copolymerisation von Kohlendioxid mit 1.2-Epoxypropan in welcher die Ringoffnung an der Methylen-Sauerstoff-Bindung stattfindet.

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Stereochemistry of some derivatives of phenylcyclohexane

Cited by 24 publications

References 15 publications

Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Isomeric Mixture Analysis of Some Ring-opening Reactions of Styrene Oxide

Stereochemistry of copolymerization of optically active cyclohexylepoxyethane with carbon dioxide

Stereochemistry of the copolymerization of carbon dioxide with optically active phenylepoxyethane

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