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Nitrile Oxides, Nitrones & Nitronates in Organic Synthesis: Novel Strategies in Synthesis PDF

768 Pages·2008·5.73 MB·english
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NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS Novel Strategies in Synthesis Second Edition Edited by Henry Feuer A JOHN WILEY & SONS, INC., PUBLICATION NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS NITRILE OXIDES, NITRONES, AND NITRONATES IN ORGANIC SYNTHESIS Novel Strategies in Synthesis Second Edition Edited by Henry Feuer A JOHN WILEY & SONS, INC., PUBLICATION Copyright2008byJohnWiley&Sons,Inc.Allrightsreserved. PublishedbyJohnWiley&Sons,Inc.,Hoboken,NewJersey. PublishedsimultaneouslyinCanada. Nopartofthispublicationmaybereproduced,storedinaretrievalsystem,ortransmittedinany formorbyanymeans,electronic,mechanical,photocopying, recording,scanning,orotherwise, exceptaspermittedunderSection107or108ofthe1976UnitedStatesCopyrightAct,without eitherthepriorwrittenpermissionofthePublisher,orauthorizationthroughpaymentofthe appropriateper-copyfeetotheCopyrightClearanceCenter,Inc.,222RosewoodDrive,Danvers, MA01923,(978)750-8400,fax(978)750-4470,oronthewebat www.copyright.com.Requests tothePublisherforpermissionshouldbeaddressedtothePermissionsDepartment,JohnWiley& Sons,Inc.,111RiverStreet,Hoboken,NJ07030,(201)748-6011,fax(201)748-6008,oronlineat http://www.wiley.com/go/permission. LimitofLiability/DisclaimerofWarranty:Whilethepublisherandauthorhaveusedtheirbest effortsinpreparingthisbook,theymakenorepresentationsorwarrantieswithrespecttothe accuracyorcompletenessofthecontentsofthisbookandspeci(cid:222)callydisclaimanyimplied warrantiesofmerchantabilityor(cid:222)tnessforaparticularpurpose.Nowarrantymaybecreatedor extendedbysalesrepresentativesorwrittensalesmaterials.Theadviceandstrategiescontained hereinmaynotbesuitableforyoursituation.Youshouldconsultwithaprofessionalwhere appropriate.Neitherthepublishernorauthorshallbeliableforanylossofpro(cid:222)toranyother commercialdamages,includingbutnotlimitedtospecial,incidental,consequential,orother damages. Forgeneralinformationonourotherproductsandservicesorfortechnicalsupport,pleasecontact ourCustomerCareDepartmentwithintheUnitedStatesat(800)762-2974,outsidetheUnited Statesat(317)572-3993orfax(317)572-4002. Wileyalsopublishesitsbooksinavarietyofelectronicformats.Somecontentthatappearsinprint maynotbeavailableinelectronicformats.FormoreinformationaboutWileyproducts,visitour websiteatwww.wiley.com. WileyBicentennialLogo:RichardJ.Paci(cid:222)co LibraryofCongressCataloging-in-Publication Data: Nitrileoxides,nitrones&nitronatesinorganicsynthesis:novelstrategiesin synthesis.(cid:151)2nd ed./editedbyHenryFeuer. p.cm. Includesindex. ISBN978-0-471-74498-6 (cloth) 1.Nitrogenoxides.2.Organiccompounds(cid:151)Synthesis. I.Torssell,Kurt,1926(cid:150). Nitrileoxides,nitronesandnitronatesinorganicsynthesis.II.Feuer,Henry,1912(cid:150) III.Title:Nitrileoxides,nitronesandnitronatesinorganicsynthesis. QD305.N8N532007 547(cid:2).2(cid:151)dc22 2007024688 PrintedintheUnitedStatesofAmerica 10987654321 CONTENTS Series Foreword vii List of Abbreviations ix 1 Nitrile Oxides 1 Leonid I.Belen(cid:146)kii, N.D.ZelinksyInstitute of Organic Chemistry, Russian Academyof Sciences,119991, Moscow,Russia 2 Nitrones: Novel Strategies in Synthesis 129 Igor Alexeevich Grigor(cid:146)ev, Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academyof Sciences,630090, Novosibirsk, Russia 3 Nitronates 435 Sema L.Ioffe, N. D. ZelinskyInstitute of Organic Chemistry, 119991 MoscowGSP-1, Russia Index 749 v SERIES FOREWORD Thebeginningofaliphaticnitrochemistrygoesbackto1872whenV.Meyerand O. Stueber achieved the synthesis of 1-nitropentane by reacting 1-iodopentane with silver nitrite. This report led to an impetus of researchin the(cid:222)eld,resulting in numerous publications. Another important development in the (cid:222)eld was the discovery of the vapor- phase nitration in the 1930s by H. Hass and his students at Purdue University. It ledin1940tothecommercialproductionoflowermolecularweightnitroalkanes [C1 to C4] at a pilot plant of the Commercial Solvents Corporation in Peoria, Illinois. In the organic nitro chemistry era of the (cid:222)fties and early sixties, a great emphasis of the research was directed towards the synthesis of new compounds that would be useful as potential ingredients in explosives and propellants. In recent years, the emphasis of research has been directed more and more toward utilizing nitro compounds as reactive intermediates in organic synthe- sis. The activating effect of the nitro group is exploited in carrying out many organic reactions, and its facile transformation into various functional groups has broadened the importance of nitro compounds in the synthesis of complex molecules. It is the purpose of the series to review the (cid:222)eld of organic nitro chemistry in its broadest sense by including structurally related classes of compounds such as nitroamines, nitrates, nitrones and nitrile oxides. It is intended that the con- tributors, who are active investigators in various facets of the (cid:222)eld, will provide a concise presentation of recent advances that have generated a renaissance in nitro chemistry research. Inthismulti-authoredvolumearepresentedtheimportanttopicsofnitronates, nitrones and nitrile oxides. Their signi(cid:222)cance in synthesis as starting materials and as reactive intermediates has grown considerably since 1988 in which year Dr. Torssell(cid:146)s monograph was published by Wiley-VCH. Henry Feuer Purdue University vii

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