The Stereoisomerism of Cyclohexane Derivatives.

Orloff, Harold D.

doi:10.1021/cr60169a001

Cited by 66 publications

(22 citation statements)

References 190 publications

(311 reference statements)

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“…Menthol is also used as a test molecule for structure elucidation by NMR (nuclear magnetic resonance) [8]. As a cyclohexane derivative, its stereochemical analysis has been the focus of research since decades [9]. Although computational chemistry has contributed a lot to our present knowledge, it is still mandatory to use experimental information for an accurate conformational analysis of cyclohexanes [10].…”

Section: Introductionmentioning

confidence: 99%

Stereochemical analysis of menthol and menthylamine isomers using calculated and experimental optical rotation data

Reinscheid

2016

Journal of Molecular Structure

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a b s t r a c tThe complete series of menthol isomers and their corresponding amino derivatives (base and protonated/HCl forms), were investigated using experimental and theoretical data. Our study focused on the conformational and configurational analysis, and revealed that experimental data should be used in combination with calculated data. Furthermore, even in the case of the highly studied member, menthol, discrepancies were found among previously published literature values. We show that the correct determination of the population mix is a must for the correct prediction of the absolute configuration (AC) of neoisomenthol. The neoiso forms are of special interest since a number of structural inconsistences can be found in the literature. We present a stringent proof of the AC of neoisomenthol based on literature information. To the best of our knowledge, the AC of neoisomenthylamine is for the first time shown using experimental and calculated optical rotation data. A correction of a series of publications containing an important error in the assignment of (þ)-menthylamine (correct: (þ)-neomenthylamine) is presented. With 26 data pairs (experimental versus calculated) of optical rotation values a regression is performed. The AC of all 12 compounds, even the most difficult neoiso forms, could be predicted correctly using experimental low-temperature NMR data. Furthermore, if only experimental data with an optical rotation outside the range of À10 < [a] > þ10 are used, all 12 compounds would have been correctly assigned without lowtemperature NMR data as restraints.

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Section: Introductionmentioning

confidence: 99%

Stereochemical analysis of menthol and menthylamine isomers using calculated and experimental optical rotation data

Reinscheid

2016

Journal of Molecular Structure

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“…The structures of BHC isomers were studied using the electron diffraction method, which established a scientific basis for the modern conformational theory of Orloff [14], and Hassel and colleagues [15]. Furthermore, the chair conformation of BHC isomers was determined by X-ray analyses of α-BHC [15].…”

Section: Discovery Of Bhc and Its Chemical Structures And Propertiesmentioning

confidence: 99%

γ-BHC: Its history and mystery – why is only γ-BHC insecticidal?

Tanaka

2015

Pesticide Biochemistry and Physiology

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“…The crude extract, thus obtained is a mixture of stereoisomers. Of the 16 theoretically possible stereoisomers of HCH, chain interconversions reduce the number to only eight [97]. Out of them, four isomers viz.…”

Section: Isomerizationmentioning

confidence: 99%

Genetic manipulations of microorganisms for the degradation of hexachlorocyclohexane

Johri

1996

FEMS Microbiology Reviews

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Hexachlorocyclohexane (HCH) is an organochlorine insecticide which has been banned in technologically advanced countries. However, it is still in use in tropical countries for mosquito control and thus new areas continue to be contaminated. Anaerobic degradation of HCH isomers have been well documented but until recently there have been only a few reports on aerobic microbial degradation of HCH isomers. The isolation of these microbes made it possible to design experiments for the cloning of the catabolic genes responsible for degradation. We review the microbial degradation of HCH isomers coupled with the genetic manipulations of the catabolic genes. The first part discusses the persistence of residues in the environment and microbial degradation while the second part gives an account of the genetic manipulations of catabolic genes inw)lved in the degradation.

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The Stereoisomerism of Cyclohexane Derivatives.

Cited by 66 publications

References 190 publications

Stereochemical analysis of menthol and menthylamine isomers using calculated and experimental optical rotation data

Stereochemical analysis of menthol and menthylamine isomers using calculated and experimental optical rotation data

γ-BHC: Its history and mystery – why is only γ-BHC insecticidal?

Genetic manipulations of microorganisms for the degradation of hexachlorocyclohexane

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