{"title":"Polyhalogenoaromatic compounds. Part XIX. Metal–halogen exchange reactions of n-butyl-lithium with tetrabromo-4-pyridyl and tetrachloro-2-pyridyl derivatives","authors":"D. Berry, B. Wakefield, J. D. Cook","doi":"10.1039/J39710001227","DOIUrl":"https://doi.org/10.1039/J39710001227","url":null,"abstract":"The reaction of n-butyl-lithium with tetrabromo-4-methoxypyridine, tetrabromo-4-dimethylaminopyridine, and tetrabromo-4-piperidinopyridine led to the corresponding tribromo-3-pyridyl-lithium derivatives. When heated in the presence of furan, tribromo-4-methoxy-3-pyridyl-lithium gave an adduct of 5,6-dibromo-4-methoxy-2-pyridine. The reaction of n-butyl-lithium with tetrachloro-6-methoxypyridine, tetrachloro-6-dimethylamino-pyridine, tetrachloro-6-pyrrolidinopyridine and tetrachloro-6-piperidinopyridine led to the corresponding trichloro-4-pyridyl-lithium derivatives. When heated in the presence of furan, each of these lithium compounds gave only one of the two possible pyridyne adducts; evidence is presented that the 2-substituted 3-pyridyne was involved in each case. Factors governing the position of metal–halogen exchange in polyhalogeno-benzenes and -pyridines are discussed.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"21 1","pages":"1227-1231"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80578336","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}
{"title":"Calciferol and its relatives. Part XV. The preparation of des-AB-cholest-8-ene-8-carbaldehyde {1?-[(1R)-1,5-dimethylhexyl]-3a?,6,7,7a?-tetrahydro-7a?-methylindane-4-carbaldehyde} and 9?-chloro-des-AB-cholestan-8-one {5?-chloro-1?-[(1R)-1,5-dimethylhexyl]-7a?-methyl-trans-perhydroindan-4-one}","authors":"P. Littlewood, B. Lythgoe, A. Saksena","doi":"10.1039/j39710002955","DOIUrl":"https://doi.org/10.1039/j39710002955","url":null,"abstract":"Several des-AB-cholestane derivatives, carrying oxygen functions at position 8 or 9, or both, are prepared from des-AB-cholest-8-ene or from des-AB-cholestane-8β,9α-diol. They include the two title compounds, required for the total synthesis of tachysterol3 and precalciferol3, respectively.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"181 1","pages":"2955"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"80684952","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}
{"title":"Acenaphthene. Part II. The preparation of 3,4-diaminonaphthalene-1,8-dicarboxylic anhydride (3,4-diaminonaphthalic anhydride) and derivatives","authors":"L. A. Jones, H. K. Kim, R. Watson","doi":"10.1039/J39710003891","DOIUrl":"https://doi.org/10.1039/J39710003891","url":null,"abstract":"The synthesis of the previously unknown 3,4-diaminonaphthalene-1,8-dicarboxylic anhydride (7) is reported. Support for the structural assignment is found in an alternate synthetic route to the dialkyl esters (16) and (17). All new compounds are characterized by elemental analysis and i.r. and n.m.r. spectroscopy.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"238 1","pages":"3891-3893"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79706851","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}
{"title":"Benzopyrones. Part III. Synthesis and mass spectra of some oxopyranobenzoxazolecarboxylic esters","authors":"G. Barker, G. P. Ellis","doi":"10.1039/J39710001482","DOIUrl":"https://doi.org/10.1039/J39710001482","url":null,"abstract":"The preparation of ethyl 8-amino-7-hydroxy-4-oxochromen-2-carboxylate (1) and two of its isomers from the corresponding nitro-compounds is described. Cyclization of the Schiff bases from these amino-phenols and various nitrobenzaldehydes gave the oxopyranobenzoxazoles (4)–(7). The amino-phenols (1) and (2) were also cyclized by use of phosgene or thiophosgene to give the corresponding oxo- or thioxo-oxazoles (8)–(11). The mass spectra of 2-phenylbenzoxazole (12) and benzoxazol-2(3H)-one (13) are interpreted. A similar study of the pyranobenzoxazoles (4)–(11) showed fragmentation patterns characteristic of chromones rather than of benzoxazoles.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"349 1","pages":"1482-1484"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"79718007","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}
D. E. Grocock, T. K. Jones, G. Hallas, J. Hepworth
{"title":"Metallation of 1,3-bistrifluoromethylbenzene and NN-dimethyl-3,5-bistrifluoromethylaniline","authors":"D. E. Grocock, T. K. Jones, G. Hallas, J. Hepworth","doi":"10.1039/J39710003305","DOIUrl":"https://doi.org/10.1039/J39710003305","url":null,"abstract":"The metallation of 1,3-bistrifluoromethylbenzene with the n-butyl-lithium–NNN′N′-tetramethylethylenediamine complex occurs essentially only at the 2-position, but with n-butyl-lithium alone a mixture of products results. n-Butyl-lithium reacts with NN-dimethyl-3,5-bistrifluoromethylaniline mainly at the 4-position. Treatment of 3,5-bistrifluoromethylaniline with aqueous bromine gives a dibromo-compound. Structures are assigned on the basis of 1H n.m.r. data.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"203 1","pages":"3305-3308"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"83426023","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}
{"title":"Nuclear magnetic resonance evidence regarding the stereochemistry of some cyanoindanylidene compounds","authors":"A. Bahl, W. Kemp","doi":"10.1039/J39710001583","DOIUrl":"https://doi.org/10.1039/J39710001583","url":null,"abstract":"The n.m.r. spectra of a series of indane derivatives with an exocyclic double bond have been examined, and the stereochemistry of such compounds deduced from chemical-shift data. Stereochemical assignments extend, and are different from, those previously reported.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"24 1","pages":"1583-1585"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84654515","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}
{"title":"1,2,3-Benzothiadiazoles. Part IV. The rearrangement of diazonium salts derived from 7-aminobenzothiazoles","authors":"E. Haddock, P. Kirby, A. Johnson","doi":"10.1039/J39710003642","DOIUrl":"https://doi.org/10.1039/J39710003642","url":null,"abstract":"The rearrangement of the diazonium salts of 7-aminobenzothiazoles to derivatives of 7-amino-1,2,3-benzothiadiazole is shown to proceed through 7-acylamino-1,2,3-benzothiadiazoles.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"11 1","pages":"3642-3644"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87322583","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}
{"title":"Synthesis of corydalactam","authors":"T. Kametani, M. Ihara*","doi":"10.1039/J39710000999","DOIUrl":"https://doi.org/10.1039/J39710000999","url":null,"abstract":"","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"48 3 1","pages":"999-1000"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"84706805","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}
{"title":"The acetolysis and benzolysis of some carbohydrate oxirans","authors":"J. Buchanan, J. Conn, A. Edgar, R. Fletcher","doi":"10.1039/J39710001515","DOIUrl":"https://doi.org/10.1039/J39710001515","url":null,"abstract":"A cyclic acyloxonium ion is formed as an intermediate when a carbohydrate oxiran bearing a vicinal trans-acyloxy-group is heated in acetic acid. In the presence of water the cyclic ion yields a cis-monoester. Under anhydrous conditions, using acetic acid or molten benzoic acid as solvent, three products are generally formed, corresponding to nucleophilic attack at each of the three carbon atoms of the cyclic ion. Possible mechanisms are discussed in the light of other published work on the properties of acyloxonium ions derived from polyols.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"126 1","pages":"1515-1521"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88161478","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}
{"title":"Partially fluorinated heterocyclic compounds. Part IX. The syntheses of 4,5,6,7-tetrafluorobenzo[b]furan and 4,5,6,7-tetrafluoro-2-phenylbenzo[b]furan by a new cyclisation reaction, and the attempted syntheses of related compounds by conventional methods","authors":"G. Brooke, W. Musgrave, T. R. Thomas","doi":"10.1039/J39710003596","DOIUrl":"https://doi.org/10.1039/J39710003596","url":null,"abstract":"4,5,6,7-Tetrafluorobenzo[b]furan and 4,5,6,7-tetrafluoro-2-phenylbenzo[b]furan have been prepared by the sodium hydride-induced cyclisation of (pentafluorophenyl)acetaldehyde and 2-(pentafluorophenyl) acetophenone, respectively. Attempted cyclisation of ethyl (2-ethoxycarbonyl-3,4,5,6-tetrafluorophenoxy) fluoroacetate and of 2′,3′,4′,5′,6′-pentafluoro-2-hydroxyacetophenone both failed.","PeriodicalId":17245,"journal":{"name":"Journal of The Chemical Society C: Organic","volume":"51 1","pages":"3596-3599"},"PeriodicalIF":0.0,"publicationDate":"1971-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"88457591","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}