Separation and photoinduced transformations of the enantiomers of 3′,3′-dimethylspiro[2H-1-benzopyran-2,1′(2)oxaindans]

Stephan, Barbara; Mannschreck, Albrecht; Voloshin, N. A.; Volbushko, N. V.

doi:10.1016/s0040-4039(00)97057-6

Cited by 13 publications

(3 citation statements)

References 13 publications

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“…Other examples in which the central carbon was linked to two oxygen in 2,2’‐spirochromene derivatives 7 and 2‐oxaindan spiropyrane derivatives 8 were reported by Mannschreck and colleagues . Spirochromene 7 was selected to illustrate the concept of enantiomeric enrichment of stereolabile chiral compounds by dynamic (D)HPLC .…”

Section: Resultsmentioning

confidence: 99%

A Forgotten Chiral Spiro Compound Revisited: 3,3'‐Dimethyl‐3H,3'H‐2,2'‐spirobi[[1,3]benzothiazole]

et al. 2015

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The title compound was obtained as a side product during dimerization-oxidation steps of the carbene generated from N-methylbenzothiazolium iodide. Chromatography on (S,S)-Whelk O1 column showed on cooling a typical plateau shape chromatogram indicating an exchange between two enantiomers on the column. The thermal barrier to racemization was determined (85 kJ.mol(-1) at 10 °C) by dynamic high-performance liquid chromatography (DHPLC).The absolute configuration of the first (M) and second eluted (P) enantiomers on the (S, S)-Whelk O1 column was established by comparing the reconstructed circular dichroism (CD) spectra from the CD detector signal and the calculated CD spectrum of the (P) enantiomer. Mass spectrometry revealed that 3,3'-dimethyl-3H,3'H-2,2'-spirobi[[1,3]benzothiazole] can be viewed as a masked thiophenate attached to a benzothiazolium framework.

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Section: Resultsmentioning

confidence: 99%

A Forgotten Chiral Spiro Compound Revisited: 3,3'‐Dimethyl‐3H,3'H‐2,2'‐spirobi[[1,3]benzothiazole]

et al. 2015

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“…The enantiomers of 1 ( Fig.1) were separated with the high-pressure liquid chromatography (HPLC) method [12].…”

Section: Resultsmentioning

confidence: 99%

“…An enantiomerically pure, optically active spiropyran could be the object of several interesting experiments [3,8,11,12], but laboratory procedures normally give a 1:1 mixture of both enantiomers. Successful attempts to separate the spiropyran enantiomers have already been undertaken by Mannschreck and coworkers [12 -14], but the absolute configuration of the 0932-0784 / 03 / 0700-0443 $ 06.00 c 2003 Verlag der Zeitschrift für Naturforschung, Tübingen · http://znaturforsch.com Scheme 1. stereoisomers has not been determined and still remains unknown.…”

Section: Introductionmentioning

confidence: 99%

6-Methoxy-3,3’,3’-Trimethylspiro[2H-1-Benzopyran-2,1’[2]Oxaindan]: Separation Of Enantiomers, Circular Dichroism Measurements And Determination Of The Absolute Configuration

Voloshina

Wang

Voloshina

et al. 2003

Zeitschrift Für Naturforschung A

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A quantum mechanical approach to electrochemical behavior of spirochromics

Yurtsever

Ustamehmetoğlu

Sarac

et al. 1999

Int. J. Quant. Chem.

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ABSTRACT:Fully optimized semiempirical quantum-chemical calculations of photochromic spiropyrans are presented. The vertical ionization potentials are calculated and their variation with substitutions are correlated to experimental oxidation potentials. The effects of the substitutions are studied and the partial charges on indoline and pyran components generated by HOMO are found to be responsible for the variations. The deactivating groups on the indoline ring system and deactivating groups on the pyran system increase the ionization potential and, consecutively, the oxidation potential.

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Separation and photoinduced transformations of the enantiomers of 3′,3′-dimethylspiro[2H-1-benzopyran-2,1′(2)oxaindans]

Cited by 13 publications

References 13 publications

A Forgotten Chiral Spiro Compound Revisited: 3,3'‐Dimethyl‐3H,3'H‐2,2'‐spirobi[[1,3]benzothiazole]

A Forgotten Chiral Spiro Compound Revisited: 3,3'‐Dimethyl‐3H,3'H‐2,2'‐spirobi[[1,3]benzothiazole]

6-Methoxy-3,3’,3’-Trimethylspiro[2H-1-Benzopyran-2,1’[2]Oxaindan]: Separation Of Enantiomers, Circular Dichroism Measurements And Determination Of The Absolute Configuration

A quantum mechanical approach to electrochemical behavior of spirochromics

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