Highly stereoselective chlorination of β-substituted cyclic alcohols using PPh3-NCS: Factors that control the stereoselectivity

Chemical Communications

Volumn , Issue 8, 2007, Pages 867-869

  Jaseer, E A ^a   Naidu, Ajay B ^a   Kumar, Sreehari S ^a   Rao, R Koteshwar ^a   Thakur, Krishna G ^a   Sekar, G ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; CHLORIDE; N CHLOROSUCCINIMIDE; PHOSPHOPROTEIN PHOSPHATASE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHLORINATION; ELECTRON; HALOGENATION; NEIGHBOR JOINING METHOD; STEREOCHEMISTRY;

EID: 33847050798     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b614512d     Document Type: Article

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15. Pauling scale for the electronegativity of O, N, and S: O (3.5) > N (3.0) > S (2.58). In other words, we can explain this NGP ability by the nucleophilicity of the β-substituted atoms. The nucleophilicity of O, N, and S: S > N > O
16. Allowing these reactions to continue for longer times or using excess halogenating agents did not help to improve the yield