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The γ-Alkylation and γ-Arylation of Dianions of β-Dicarbonyl Compounds β-二羰基化合物中二离子的γ-烷基化和γ-芳基化
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR017.02
T. Harris, C. Harris
{"title":"The γ-Alkylation and γ-Arylation of Dianions of β-Dicarbonyl Compounds","authors":"T. Harris, C. Harris","doi":"10.1002/0471264180.OR017.02","DOIUrl":"https://doi.org/10.1002/0471264180.OR017.02","url":null,"abstract":"It is well known that beta-diketones can undergo condensations at the alpha-methylene group with alkyl halides and certain other reagents though the intermediate formation of monoanions. For example, acetylacetone on treatment with an alkali metal or an alkali metal alkoxide or carbonate forms a mono-anion which can be alkylated with alkyl halides. In 1958, Hauser and Harris reported that, if benzoylacetone or acetylacetone is first converted to the dipotassium salt. The salt undergoes alkylation and other carbon-carbon condensations at the terminal methyl group rather than at the methylene group. Rapid alkylation was observed when the salts were treated with benzyl chloride and after acidification, the terminal monobenzylation derivatives were obtained in good yield. Dibenzylation was not observed. In this chapter alkylations of these and other beta-ketones via dianions are surveyed. Other alkylations are also discussed. Arylations are included because alkylation and arylation are methods for directly converting beta-homologs without increasing their functionality. \u0000 \u0000 \u0000Keywords: \u0000 \u0000gamma-arylation; \u0000gamma-alkylation; \u0000dianions; \u0000beta-carbonyl compounds; \u0000acetylacetone; \u0000beta-ketones; \u0000keto-aldehydes; \u0000keto-esters; \u0000dicarbonyl compounds; \u0000alkyl halides; \u0000alkylation; \u0000ammonia; \u0000experimental procedures","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"19 1","pages":"155-212"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87070362","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 1
Synthesis of Peptides with Mixed Anhydrides 混合酸酐多肽的合成
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR012.04
N. Albertson
{"title":"Synthesis of Peptides with Mixed Anhydrides","authors":"N. Albertson","doi":"10.1002/0471264180.OR012.04","DOIUrl":"https://doi.org/10.1002/0471264180.OR012.04","url":null,"abstract":"A mixed acid anhydride, or mixed anhydride, is a dehydration product of two polyoxy acids. For a mixed anhydride to be of interest for peptide synthesis, one of the components must, in general, be an alpha-acylamino acid. The nature of the second component acid may vary widely. In this chapter the term mixed anhydride will be used in a more general sense. In addition to conventional mixed anhydrides, from polyoxyacids, reference will be made to “mixed anhydrides” otherwise recognizable as acyl halides, ethers, esters, thiol esters, O-acylisoureas and isoimides. This chapter is limited to a review of chemistry of the acyclic alpha-amino acid mixed anhydrides, which the well-know alpha-acylamino acid chlorides and azides, which have been the subject of an excellent review. In general, discussion of the application of alpha-acyllamino acid mixed anhydrides will be limited to non-polymeric peptide bond formation and will not be concerned with acylations other than those that lead to a peptide bonds. \u0000 \u0000 \u0000Keywords: \u0000 \u0000peptides; \u0000mixed anhydrides; \u0000amide bond formation bis(alpha-acylaminoacyl)carbonates; \u0000alpha-acylaminoacyl chlorocarbonates; \u0000alpha-acylaminoacyl alkyl carbonates. side reactions; \u0000experimental conditions","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"35 1","pages":"157-255"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86629293","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 5
The Leuckart Reaction 琉卡特反应
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR005.07
M. L. Moore
{"title":"The Leuckart Reaction","authors":"M. L. Moore","doi":"10.1002/0471264180.OR005.07","DOIUrl":"https://doi.org/10.1002/0471264180.OR005.07","url":null,"abstract":"The Leuckart reaction is a process for reductive alkylation of ammonia or primary or secondary amines by certain aldehdyes and ketones, It is distinguished by the fact that the reduction is accomplished by formic acid or a derivative of formic acid and should be compared with reductive alkylation discussed elsewhere in this series. The reaction is carried out by heating a mixture of the carbonyl compound and the formic acid salt or formyl derivative of ammonia or the amine. Primary and secondary amines produced in the reaction often are obtained as the formyl derivatives and must be recovered by hydrolysis; tertiary amines are obtained as formate. Modifications of this reaction are discussed. \u0000 \u0000 \u0000Keywords: \u0000 \u0000Leuckart reaction; \u0000formaldehyde; \u0000aldehydes; \u0000ketones; \u0000quinones; \u0000pyrazolone; \u0000oxindole; \u0000ammonium formate; \u0000reductive alkylation. amines; \u0000experimental procedures","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"135 1","pages":"301-330"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89028206","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 14
The Preparation of Thiophenes and Tetrahydrothiophenes 噻吩和四氢噻吩的制备
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR006.09
D. Wolf, K. Folkers
{"title":"The Preparation of Thiophenes and Tetrahydrothiophenes","authors":"D. Wolf, K. Folkers","doi":"10.1002/0471264180.OR006.09","DOIUrl":"https://doi.org/10.1002/0471264180.OR006.09","url":null,"abstract":"Thiophenes and tetrahydrothiophenes are discussed as separate major divisions in this chapter because there are significant differences in the general methods by which these two similar types of compounds are prepared. The general reactions that lead to the formation of thiophenes may be segregated in the following five general classifications (1) Reaction of the 1,4-difunctional compounds with sulfides; (2) reaction of unsaturated compounds with sulfides; (3) reaction of 1,2-difunctional compounds with thiodiacetic acid and esters; (4) reaction of aryl methyl ketones with sulfides; (5) miscellaneous cyclization reactions. Similarly the reactions that form tetrahydrothiophenes may be grouped into four general classifications: (1) Reaction of 1,4-difunctional compounds with sulfides; (2) Dieckmann cyclization; (3) Catalytic method; (4) miscellaneous methods. All of the above are discussed in this chapter. \u0000 \u0000 \u0000Keywords: \u0000 \u0000thiophenes; \u0000tetrahydrothiophenes; \u0000sulfides; \u0000succinic acids; \u00001,4-Difunctional compounds; \u00001,2-Difunctional compounds; \u0000experimental procedures","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"45 1","pages":"410-468"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"90216058","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
The Rosenmund Reduction of Acid Chlorides to Aldehydes 酸氯化物的罗森蒙还原成醛
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR004.07
E. Mosettig, R. Mozingo
{"title":"The Rosenmund Reduction of Acid Chlorides to Aldehydes","authors":"E. Mosettig, R. Mozingo","doi":"10.1002/0471264180.OR004.07","DOIUrl":"https://doi.org/10.1002/0471264180.OR004.07","url":null,"abstract":"In the synthesis of complex molecules, particularly in connection with natural products, it is occasionally desirable to prepare an aldehyde when the readily available starting material is the corresponding acid. The Rosenmund reduction is probably the most useful method for application to a large number of aldehdyes of varied types. The Rosenmund reduction consists in the selective hydrogenation of an acid chloride in the presence of a suitable catalyst, usually supported palladium to the corresponding aldehyde. \u0000 \u0000 \u0000Keywords: \u0000 \u0000Rosenmund reduction; \u0000acid chlorides; \u0000aldehydes; \u0000catalyst; \u0000regulator; \u0000solvent; \u0000hydrogen; \u0000precautions; \u0000experimental procedures","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"1 1","pages":"362-377"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88841419","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
The Preparation of Aromatic Arsonic and Arsinic Acids by the Bart, Bechamp, and Rosenmund Reactions Bart, Bechamp和Rosenmund反应制备芳香族砷酸和砷酸
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR002.10
C. S. Hamilton, J. F. Morgan
{"title":"The Preparation of Aromatic Arsonic and Arsinic Acids by the Bart, Bechamp, and Rosenmund Reactions","authors":"C. S. Hamilton, J. F. Morgan","doi":"10.1002/0471264180.OR002.10","DOIUrl":"https://doi.org/10.1002/0471264180.OR002.10","url":null,"abstract":"Arsonic acids may be regarded as derived from orthoarsenic acid, by replacement of one of the hydroxyl groups with an organic residue, the arsenic acids are similarly derived by replacement of the two hydroxyl groups. The preparation of aromatic arsenic acids is described in this chapter. The most widely used is the Bart reaction, which involves the interaction of a diazonium salt with an inorganic arsenic compound. Arsenic acids are also obtained as by-products in the Bechamp synthesis. In the Rosenmund synthesis, salts of arsenic acids are obtained by treatment of aryl halides with sodium or potassium arsenite. \u0000 \u0000 \u0000Keywords: \u0000 \u0000aromatic arsenic acid; \u0000arsinic acid; \u0000Bart reaction; \u0000Bechamp reaction; \u0000Rosenmund reaction; \u0000limitations; \u0000side reactions; \u0000procedures; \u0000arsonation","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"29 1","pages":"415-454"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88949665","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 6
Cyclobutane Derivatives from Thermal Cycloaddition Reactions 热环加成反应的环丁烷衍生物
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR012.01
John D. Roberts, C. M. Sharts
{"title":"Cyclobutane Derivatives from Thermal Cycloaddition Reactions","authors":"John D. Roberts, C. M. Sharts","doi":"10.1002/0471264180.OR012.01","DOIUrl":"https://doi.org/10.1002/0471264180.OR012.01","url":null,"abstract":"Preparation of substituted cyclobutanes and cyclobutenes by cyclo-addition reactions of alkene and alkyne has become an important synthetic reaction and where applicable is the method of choice for four-membered carbon ring compounds. Such cycloadditons may be achieved thermally under autogeneous pressure in the presence of free-radical inhibitors or photochemically by irradiation with visible or ultraviolet light. The establishment of cyclobutane structure proved an example of waxing and waning in the interpretation of organic reactions. Many studies were done and they are discussed. A breakthrough came with the discovery by DuPont that octafluorocyclobutane can be formed readily by thermal dimerization of tetrafluoroethylene. Several developments followed. The cycloaddition illustrates two important points. First, fluorinated alkenes may add to non-fluorinated unsaturated compounds much more readily than they dimerize. Second, when fluorinated alkenes are given a choice between four- and six-membered rings, as is possible with a conjugated diene, the formation of the four-membered ring is favored. This chapter gives information on the various studies done on this reaction, The scope, limitations, and comparison of added reactivities are detailed.","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"94 1","pages":"1-56"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83347232","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 2
Sensitized Photooxygenation of Olefins 烯烃的感光光氧化
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR020.02
R. Denny, A. Nickon
{"title":"Sensitized Photooxygenation of Olefins","authors":"R. Denny, A. Nickon","doi":"10.1002/0471264180.OR020.02","DOIUrl":"https://doi.org/10.1002/0471264180.OR020.02","url":null,"abstract":"Sensitized photooxygenations of olefins have been extensively studied; they represent convenient methods for the introduction of oxygen at specific sites. When an aerated solution containing a monolefin, diene, or polyene, and a sensitizer is irradiated with light that can be absorbed by the sensitizer, oxygenated products are formed whose nature depends upon the structure of the substrate and the lability of the initial photoproducts under the reaction conditions. The ready reducibility of hydroperoxides to alcohols enhances the synthetic usefulness of these photoxygenations In this chapter, coverage is restricted to molecules with one or more carbon-carbon double bonds. \u0000 \u0000 \u0000Keywords: \u0000 \u0000sensitized photooxygenation; \u0000olefins; \u0000rearrangements; \u0000reduction; \u0000monoolefins; \u0000solvent effects; \u0000steric effects; \u0000electronic effects; \u0000dioxetane reaction; \u0000allylic hydroperoxides; \u00001,4-epidioxides; \u0000experimental conditions","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"26 8 1","pages":"133-336"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83503756","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 4
The Zinin Reduction of Nitroarenes 硝基芳烃的锌素还原
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR020.04
H. K. Porter
{"title":"The Zinin Reduction of Nitroarenes","authors":"H. K. Porter","doi":"10.1002/0471264180.OR020.04","DOIUrl":"https://doi.org/10.1002/0471264180.OR020.04","url":null,"abstract":"The Zinin reduction is a method for the reduction of nitroarenes by negative divalent sulfur. This versatile reaction can be carried out in the laboratory and for plant-scale manufacture of aromatic amines when other reduction media are destructive to sensitive compounds or result in undesired side reactions. The first reaction, used by Zinin, was to prepare aniline from nitrobenzene. It has been of great importance in the preparation of aromatic amines. Refinements in technique and a better understanding of the reaction mechanism should make this method attractive for the preparation of a variety of amines. \u0000 \u0000 \u0000Keywords: \u0000 \u0000zinin reduction; \u0000nitroarenes; \u0000side reactions; \u0000nitro groups. nitrosoarenes; \u0000arylamines; \u0000azobenzene reduction; \u0000hydrazobenzene; \u0000experimental conditions","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"143 1","pages":"455-481"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"86597458","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 9
Epoxidation and Hydroxylation of Ethylenic Compounds with Organic Peracids 乙烯类化合物与有机过氧化物的环氧化和羟基化反应
Organic Reactions Pub Date : 2011-03-15 DOI: 10.1002/0471264180.OR007.07
D. Swern
{"title":"Epoxidation and Hydroxylation of Ethylenic Compounds with Organic Peracids","authors":"D. Swern","doi":"10.1002/0471264180.OR007.07","DOIUrl":"https://doi.org/10.1002/0471264180.OR007.07","url":null,"abstract":"Oxiranes and alpha-glycols can be prepared from olefins by a variety of methods. One of the most important and generally applicable of these is the oxidation of ethylenic compounds with organic peracids. Depending on the peracid employed and/or operating conditions either an oxirane or an alpha-glycol can be obtained in good yield. It is important to note that the oxidation step both in epoxidation and hydroxylation reactions with organic peracids is the conversion of the olefin to the oxirane. \u0000 \u0000 \u0000Keywords: \u0000 \u0000epoxidation; \u0000hydroxylation; \u0000ethylenic compound; \u0000organic peracids; \u0000stereochemistry; \u0000experimental conditions","PeriodicalId":19539,"journal":{"name":"Organic Reactions","volume":"27 1","pages":"378-434"},"PeriodicalIF":0.0,"publicationDate":"2011-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"75414555","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 12
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