Advances in Heterocyclic Chemistry, Volume 61 by Alan R. Katritzky

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By Alan R. Katritzky

Demonstrated in 1960, Advances in Heterocyclic Chemistry is the definitive serial within the area-one of serious significance to natural chemists, polymer chemists, and such a lot organic scientists. each 5th quantity ofAdvances in Heterocyclic Chemistry encompasses a cumulative topic index.

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Efforts were conducted to analyze the enantiomers by chiral GC analysis using a permethylated cyclodextrin CP-Chirasil-DEX CB (b-PMCD). The (À)-S form was eluted first. 5 m) capillary column (115–130 min). GC should not be recommended for analysis. However, an interesting result gained from GC analysis was the observation of partial racemization, which depended on the injector temperature. At 140  C no racemization occurred whereas at 220  C 9% of the (À) enantiomer was observed when a pure (+) 50 Ibon Alkorta et al.

The chirality is preserved at higher reaction temperatures. A cyclic “ansa” intermediate Atropisomerism and Axial Chirality in Heteroaromatic Compounds 53 resulting from the reaction of (Ph)3P+-C(Cl2)-P+(Ph)3 with the diol would be formed at room temperature leading to these unexpected results (97JCS(CC)551). Curiously “ansa” compounds that were prepared with different bridge lengths and characterized by X-rays did not show fast racemization. They were resolved by chiral chromatography (96JOC710).

As an example 3-(2-methoxyphenyl)-4-methyl-1,3-thiazole2(3H)-thione atropisomers give an opposite sign of optical rotation in acetonitrile or EtOH (03JC(A995)79). For the majority of the enantiomers (including atropisomers), the optical rotation magnitude decreases when the wavelength increases. In that case the observed sign will be the same whatever the wavelength at which the polarimeter is operating. In the case of a Cotton effect the magnitude and the sign of the optical rotation might vary with the wavelength for the same enantiomer (03JC(A995)79).

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