Persistent Link:
http://hdl.handle.net/10150/187736
Title:
PREPARATION AND REACTION OF SEVERAL DELOCALIZED DICARBANIONS.
Author:
OGLE, CRAIG ALAN.
Issue Date:
1982
Publisher:
The University of Arizona.
Rights:
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.
Abstract:
The literature on preparation and oxidation of carbanions is reviewed. Attempted preparation of many new carbanions, using Lochmann's base (potassium t-butoxide/n-butyllithium), is described; dianions 59, 76, and 85 were prepared for the first time. Preparation of 85, calculated to have the least delocalization energy of all six-carbon acyclic carbanions, completes the series of six-carbon acyclic dianions. Reaction of these and three other dicarbanions (o-48, m-58, and p-58) with dihalides and oxidizing agents were investigated. The shortest routes to certain {n}- and {n,n}-cyclophanes resulted. Good yields were obtained of {9}- and -metacyclophane. Several {n}-2,6-pyridinophanes were synthesized from dianion 59. {6,6}- and {7,7}-metacyclophane and {5,5}-, {7,7}-, and {9,9}- orthocyclophane were synthesized for the first time.
Type:
text; Dissertation-Reproduction (electronic)
Keywords:
Carbanions -- Synthesis.
Degree Name:
Ph.D.
Degree Level:
doctoral
Degree Program:
Chemistry; Graduate College
Degree Grantor:
University of Arizona

Full metadata record

DC FieldValue Language
dc.language.isoenen_US
dc.titlePREPARATION AND REACTION OF SEVERAL DELOCALIZED DICARBANIONS.en_US
dc.creatorOGLE, CRAIG ALAN.en_US
dc.contributor.authorOGLE, CRAIG ALAN.en_US
dc.date.issued1982en_US
dc.publisherThe University of Arizona.en_US
dc.rightsCopyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.en_US
dc.description.abstractThe literature on preparation and oxidation of carbanions is reviewed. Attempted preparation of many new carbanions, using Lochmann's base (potassium t-butoxide/n-butyllithium), is described; dianions 59, 76, and 85 were prepared for the first time. Preparation of 85, calculated to have the least delocalization energy of all six-carbon acyclic carbanions, completes the series of six-carbon acyclic dianions. Reaction of these and three other dicarbanions (o-48, m-58, and p-58) with dihalides and oxidizing agents were investigated. The shortest routes to certain {n}- and {n,n}-cyclophanes resulted. Good yields were obtained of {9}- and -metacyclophane. Several {n}-2,6-pyridinophanes were synthesized from dianion 59. {6,6}- and {7,7}-metacyclophane and {5,5}-, {7,7}-, and {9,9}- orthocyclophane were synthesized for the first time.en_US
dc.typetexten_US
dc.typeDissertation-Reproduction (electronic)en_US
dc.subjectCarbanions -- Synthesis.en_US
thesis.degree.namePh.D.en_US
thesis.degree.leveldoctoralen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.disciplineGraduate Collegeen_US
thesis.degree.grantorUniversity of Arizonaen_US
dc.identifier.proquest8217446en_US
dc.identifier.oclc681968262en_US
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