Adipic Acid by Ozonolysis of Cyclohexene

Bailey, Philip S.

doi:10.1021/ie50583a024

Cited by 20 publications

(11 citation statements)

References 9 publications

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“…Liquid olefinic reactants were reagent grade or purified by distillation prior to use. Pentane used as reaction solvent was purified by stirring over concentrated H0SO4 for a minimum of 24 hr, washed with saturated aqueous NaHCCL and then with water, dried (MgSOj), and distilled. Ethyl allvlnitrosocarbamate,19 diazoethane,20 cupric trifluoromethanesulfonate,21 , ethyl diazoacetate,22 isomeric ethyl 2,3-dimethylcyclopropanecarboxylates,12 and isomeric 7-carboethoxybicyclo[4.1.0]hep-tanes12 were prepared by known procedures.…”

Section: Methodsmentioning

confidence: 99%

Vinylcyclopropanation of olefins with vinyldiazomethane

Salomon¹,

Salomon²,

Heyne³

1975

J. Org. Chem.

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Vinylcyclopropanation of olefins by copper-catalyzed reaction with vinyldiazomethane is a short and convenient synthesis of vinylcyclopropanes. Though all copper salts examined cause decomposition of vinyldiazomethane with evolution of nitrogen, only a very few catalyze cyclopropanation. With cisand frams-2-butenes, the catalyzed vinylcyclopropanation is stereospecific. Several pairs of isomeric vinylcyclopropanes were prepared and

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Section: Methodsmentioning

confidence: 99%

Vinylcyclopropanation of olefins with vinyldiazomethane

Salomon¹,

Salomon²,

Heyne³

1975

J. Org. Chem.

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“…Two possible ways to obviate pyrrolidinol formation were to protect the amide nitrogen or to convert the olefin to a carboxylic acid in one step. However, the simpler compound 20 was unreactive toward protection of the carbamate nitrogen with Cbz-Cl or Boc 2 O and it could not be transformed into a carboxylic acid by NaIO 4 /KMnO 4 , NaIO 4 /RuCl 3 , or O 3 /H 2 O 2 …”

Section: Resultsmentioning

confidence: 99%

Synthesis and Conformational Analysis of the Multidrug Resistance-Reversing Agent Hapalosin and Its Non-N-methyl Analog

Dinh

Armstrong

1996

J. Org. Chem.

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Hapalosin was initially synthesized by macrolactonization, and a second synthesis was achieved by cycloamidation. In both syntheses, three of the five stereocenters in hapalosin were established by two Brown allylboration reactions. The synthesis of the non-N-Me analog of hapalosin involved chelation-controlled reduction of a gamma-amino-beta-keto ester and cycloamidation. In CDCl(3) at 25 degrees C, synthetic hapalosin exists as a 2.3:1 mixture of conformers, while its non-N-Me analog exists only as a single conformer. (1)H,(1)H-NOESY and computation reveal that the configuration of the amide bond is responsible for the conformations of the two compounds. The major conformer of hapalosin is found to be an s-cis amide, the minor conformer an s-trans amide, and the non-N-Me analog an s-trans amide. Applying distance constraints to protons that exhibit NOESY correlations, computation shows that the major conformer of hapalosin and the non-N-Me analog have very different conformations. By contrast, the minor conformer of hapalosin and the non-N-Me analog have very similar conformations.

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“…Threoand erythro-9,10-dihydroxystearic acid were converted to triols by base-catalyzed reaction with ethylene oxide at 7 psi and 180C, in an apparatus previously described (3). The reaction is summa- As with simple carboxylie acids (4,5), it is considered that the acid group is consumed in the first stages of reaction with ethylene oxide, to form ethylene glycol monoesters. With additional ethylene oxide, reaction presumably continues to a larger extent at the fl-oxyethanol and to a smaller extent at the vicinal secondary glycol functions, still disfavored by comparatively low acidities (3).…”

Section: Xyethylation Of Dihydroxystearic Acidsmentioning

confidence: 99%

“…Acids, aldehydes, or alcohols may be produced in a two-stage process, the first of which involves reaction with ozone and the second, oxidation or reduction of the ozonotysis products. As methods and processes have become more refined, however, ozonolysis has been severely criticized because of numerous byproduct reactions (5,6,13,14,23,26,28,(30)(31)(32). Consequently, ozonolysis is stated to be unsatisfactory as a method for determining the position of double bonds because of secondary reactions of the ozonide (30), because of artifacts produced (6), or even because of double bond migration during ozonolysis (7).…”

Section: Introduction Smentioning

confidence: 99%

“…It is also apparent that certain specific reagents are needed for the seeond stage in the overall ozonization reaction. For example, performie acid is superior to peracetie in oxidative treatment of cyelohexene ozonolysis products (5). Reduction by zinc and acetic acid is superior to catalytic hydrogenation in the preparation of aldehydes from methyl oleate (24).…”

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confidence: 99%

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Reactions of methoxy hydroperoxides derived from methyl oleate. Catalytic hydrogenation

Pryde

Awl

Cowan

1965

J Americ Oil Chem Soc

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Yield improvements in carbonyl compounds Obtained by catalytic hydrogenation of methyl oleate ozonolysis products have been achieved by use of catalyst poisons and by the proper choice of catalyst support. Byproduct dimethyl azelate fornmtion with palladium on charcoal was about 20% in the absence of a poison; 10%, with sodium acetate present in the support; 8%, with triethyl amine in solution. Palladium on caleimn carbonate-lead acetate gave about 7%, palladimn on zinc oxide with pyridine or lead acetate present gave 9%. The literature is reviewed on the catalytic hydrogenation of methoxy hydroperoxides derived from ozonolyses in methanol. AbstractThreoand erythro-9,10-dihydroxystearic acids

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Adipic Acid by Ozonolysis of Cyclohexene

Cited by 20 publications

References 9 publications

Vinylcyclopropanation of olefins with vinyldiazomethane

Vinylcyclopropanation of olefins with vinyldiazomethane

Synthesis and Conformational Analysis of the Multidrug Resistance-Reversing Agent Hapalosin and Its Non-N-methyl Analog

Reactions of methoxy hydroperoxides derived from methyl oleate. Catalytic hydrogenation

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