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Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl

The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ con...

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Main Author: Lee, Kheng H.
Format: Article
Published: Elsevier 1970
Subjects:
Q Science (General)
QD Chemistry
Online Access:http://eprints.um.edu.my/24697/
https://doi.org/10.1016/S0040-4020(01)92979-5
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spelling my.um.eprints.246972021-03-09T00:49:24Z http://eprints.um.edu.my/24697/ Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl Lee, Kheng H. Q Science (General) QD Chemistry The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ constant was found to differ from the value (-0·74) previously reported for BrCCl3. Different selectivity values were obtained for I and BrCCl3 toward benzaldehyde, ethylbenzene, benzyl methyl ether, benzhydryl methyl ether, and benzyl benzhydryl ether. These results indicate that the CCl3SO2 radical is mainly responsible for benzylic hydrogen-abstraction. © 1970. Elsevier 1970 Article PeerReviewed Lee, Kheng H. (1970) Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl. Tetrahedron, 26 (5). pp. 1503-1507. ISSN 0040-4020 https://doi.org/10.1016/S0040-4020(01)92979-5 doi:10.1016/S0040-4020(01)92979-5
institution Universiti Malaya
building UM Library
collection Institutional Repository
continent Asia
country Malaysia
content_provider Universiti Malaya
content_source UM Research Repository
url_provider http://eprints.um.edu.my/
topic Q Science (General)
QD Chemistry
spellingShingle Q Science (General)
QD Chemistry
Lee, Kheng H.
Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
description The relative rates of chlorination of substituted benzaldehydes with CCl3SO2Cl (I) have been determined in dilute CCl4 solution at 80° by means of competitive reactions using p-diethylbenzene as reference standard. A polar effect (ρ{variant} = -0·54) correlated by the Hammett equation with the σ constant was found to differ from the value (-0·74) previously reported for BrCCl3. Different selectivity values were obtained for I and BrCCl3 toward benzaldehyde, ethylbenzene, benzyl methyl ether, benzhydryl methyl ether, and benzyl benzhydryl ether. These results indicate that the CCl3SO2 radical is mainly responsible for benzylic hydrogen-abstraction. © 1970.
format Article
author Lee, Kheng H.
author_facet Lee, Kheng H.
author_sort Lee, Kheng H.
title Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
title_short Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
title_full Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
title_fullStr Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
title_full_unstemmed Polar effects in hydrogen abstraction from benzaldehydes—II : Radical chlorination by CCl3SO2Cl
title_sort polar effects in hydrogen abstraction from benzaldehydes—ii : radical chlorination by ccl3so2cl
publisher Elsevier
publishDate 1970
url http://eprints.um.edu.my/24697/
https://doi.org/10.1016/S0040-4020(01)92979-5
_version_ 1693726412135989248
score 13.211869

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