The current state of positive halogenating agents

Berliner, Ernst

doi:10.1021/ed043p124

Cited by 32 publications

(31 citation statements)

References 44 publications

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“…The rate of ionization of the endo-brosylate was considered normal, since its reactivity was comparable to that of cyclohexyl brosylate. Elaborating on a suggestion made earlier concerning rearrangement of camphene hydrochloride, 119 Winstein proposed that ionization of the exo-brosylate was assisted by 117 Carbon 6, which bears two hydrogens, is pentacoordinate. Attack by acetate at C(l) or C (2) is equally likely and produces equal amounts of enantiomeric acetates.…”

Section: Nonclassical Carbonium Ions and The Norbornyl Cation Problemmentioning

confidence: 97%

“…It can be estimated that the equilibrium concentration of Cl+ = 10-40 M, far too low to account for the observed reaction rate. 119 The implication of ChO as the active chlorinating species permits an alternative explanation of the established fact that chlorination proceeds in part by a process that is independent of the concentration of the aromatic reagent.…”

Section: Rate = K[arh][ch][alch]mentioning

confidence: 99%

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Advanced Organic Chemistry

1995

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Section: Nonclassical Carbonium Ions and The Norbornyl Cation Problemmentioning

confidence: 97%

Section: Rate = K[arh][ch][alch]mentioning

confidence: 99%

Advanced Organic Chemistry

1995

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“…The rate of ionization of the endo-brosylate was considered normal, since its reactivity was comparable to that of cyclohexyl brosylate. Elaborating on a suggestion made earlier concerning rearrangement of camphene hydrochloride, 119 Winstein proposed that ionization of the exo-brosylate was assisted by 117 2) bond. The plane of symmetry is seen more easily in an alternative, but equivalent, representation: Carbon 6, which bears two hydrogens, is pentacoordinate.…”

Section: Nonclassical Carbonium Ions and The Norbornyl Cation Problemmentioning

confidence: 98%

Advanced Organic Chemistry

1995

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All rights reservedNo part of this book may be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, microfilming, recording, or otherwise, without written permission from the Publisher v VI PREFACE TO PART A whose work fell into this category, we extend our apologies and request their understanding of our attempts to produce a working text, rather than to review the historical development of various concepts and techniques.This volume is a companion to Part B, Reactions and Synthesis. Part B emphasizes the synthetically important organic reactions. It adds some further mechanistic information, but is aimed primarily at introducing to students the available repertoire of organic reactions and providing an opportunity to develop a background in synthetic methodology.We believe that Parts A and B used sequentially as texts in a one-year advanced course will prepare the student to turn to the extensive review and monograph literature and to the primary journals with a thorough exposure to both the mechanistic and synthetic areas of organic chemistry.

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“…The exact mechanism involved in chlorination of organic species by hypochlorous acid has been the subject of considerable conjecture during the past 30 years and several excellent reviews have been written on the subject (77,78). Chlorination studies with hypochlorous acids have been carried out under a variety of conditions making it difficult to decide on a unique mechanism.…”

Section: Chlorination Mechanisms Of Organic Compoundsmentioning

confidence: 99%

Environmental health sciences center task force review on halogenated organics in drinking water

Deinzer¹,

Schaumburg²,

Klein³

1978

Environ Health Perspect

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The disinfection of drinking water by chlorination has in recent years come under closer scrutiny because of the potential hazards associated with the production of stable chlorinated organic chemicals. Organic chemical contaminants are common to all water supplies and it is now well-established that chlorinated by-products are obtained under conditions of disinfection, or during tertiary treatment of sewage whose products can ultimately find their way into drinking water supplies. Naturally occurring humic substances which are invariably present in drinking waters are probably the source of chloroform and other halogenated methanes, and chloroform has shown up in every water supply investigated thus far. The Environmental Protection Agency is charged with the responsibility of assessing the public health effects resulting from the consumption of contaminated drinking water. It has specifically undertaken the task of determining whether organic contaminants or their chlorinated derivatives have a special impact, and if so, what alternatives there are to protect the consumer against bacterial and viral diseases that are transmitted through infected drinking waters. The impetus to look at these chemicals is not entirely without some prima facie evidence of potential trouble. Epidemiological studies suggested a higher incidence of cancer along the lower Mississippi River where the contamination from organic chemicals is particularly high. The conclusions from these studies have, to be sure, not gone unchallenged. The task of assessing the effects of chemicals in the drinking water is a difficult one. It includes many variables, including differences in water supplies and the temporal relationship between contamination and consumption of the finished product. It must also take into account the relative importance of the effects from these chemicals in comparison to those from occupational exposure, ingestion of contaminated foods, inhalation of polluted air, and many others. The susceptibility of different age, genetic, and ethnic groups within the population must also be carefully considered. The present review discusses: the reasons for disinfection; the general occurrence of chlorinated organics in drinking water; the chemistry in the synthesis of chlorinated organics under aqueous conditions; and alternatives to chlorine for disinfection.

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The current state of positive halogenating agents

Abstract: Examines the current state of brominations, chlorinations, and iodinations, as well as kinetic evidence for the existence of unusual halogenating species.

Cited by 32 publications

References 44 publications

Advanced Organic Chemistry

Advanced Organic Chemistry

Advanced Organic Chemistry

Environmental health sciences center task force review on halogenated organics in drinking water

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