Octane Series Research Articles

The chemistry of bicyclic bisureas. 3. The synthesis and hydrolytic stability of the difluoroborate salts of 3,7-diethoxy-2,6-diaza-4,8-diazoniabicyclo[3.3.0]octane-3,7-dienes and 3,7-diethoxy-2,6-diaza-4,8-diazoniabicyclo[3.3.1]non-ane-3,7-dienes

1. Unsubstituted and tetra-N-methyl-substituted bicyclic bisureas (BBU) of the octane and nonane series on reaction with triethyloxonium fluoroborate form O-alkylation products at both carbonyl groups, namely the difluoroborates of 3,7-diethoxy-2,6-diaza-4,8-diazoniabicyclo[3.3.0]octane-3,7-dienes and 3,7-diethoxy-2,6-diaza-4,8-diazoniabicyclo[3.3.1]nonane-3,7-dienes. 2. On hydroylsis of the O-alkylation products of tetra-N-methyl-substituted BBU, the reaction resulting in the fission of one of the rings predominates.

The unambiguous synthesis of lignans of the 2,6-diaryl-3,7-dioxabicyclo-[3.3.0]octane series. The synthesis of eudesmin and 4,8-dihydroxysesamin.

The syntheses of two lignans are described. The syntheses are based on dilactones of unambiguous structure and proceed in such a way that ring opened intermediates are not involved and structures can be unequivocally assigned.

ChemInform Abstract: CHEMISTRY OF THE 6,8‐DIOXABICYCLO(3.2.1)OCTANE SERIES. SOURCES, SYNTHESES, STRUCTURES AND REACTIONS

Chemischer InformationsdienstVolume 8, Issue 23 Heterocyclic Compounds ChemInform Abstract: CHEMISTRY OF THE 6,8-DIOXABICYCLO(3.2.1)OCTANE SERIES. SOURCES, SYNTHESES, STRUCTURES AND REACTIONS B. P. MUNDY, B. P. MUNDYSearch for more papers by this authorK. B. LIPKOWITZ, K. B. LIPKOWITZSearch for more papers by this authorG. W. DIRKS, G. W. DIRKSSearch for more papers by this author B. P. MUNDY, B. P. MUNDYSearch for more papers by this authorK. B. LIPKOWITZ, K. B. LIPKOWITZSearch for more papers by this authorG. W. DIRKS, G. W. DIRKSSearch for more papers by this author First published: June 7, 1977 https://doi.org/10.1002/chin.197723265Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume8, Issue23June 7, 1977 RelatedInformation

Mass-spectrometric study of hydrocarbons of bicyclo[3.2.1]octane series

1. 1. Mass-spectra of 33 methyl-, dimethyl- and ethyl-substituted bicyclo[3.2.1]octane geomers were studied. 2. 2. Main trends of the breakdown of M + ions of bicyclo[3.2.1]octanes are due to bond ruptures at tertiary and quaternary carbon atoms. These ruptures are often accompanied by the migration of hydrogen atoms. 3. 3. Some agreement between the relative thermodynamic stability of stereo-isomers of a given structure and their resistance to electron impact was established. 4. 4. “Unfavourable” interactions of substituents with each other and with the system of bicyclo [3.2.1] octane determine the main directions of breakdown of molecular ions, while methyl substituents are retain d in neutral or charged fragments.

Chemistry of the 6,8-Dioxabicyclo[3.2.1]octane Series. Sources, Synthesis, Structures and Reactions

Chemistry of the 6,8-Dioxabicyclo[3.2.1]octane Series. Sources, Synthesis, Structures and Reactions

Carbon‐13 chemical shifts of bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives

Abstract13C chemical shifts of more than fifty bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane derivatives (hydrocarbons, alcohols, ketones and esters) have been determined. The usefulness of ethyl derivatives for the assignment of close 13C chemical shifts in bicyclic methyl derivatives is shown both for the bicyclo[3.2.1]octane and bicyclo[2.2.1]heptane series. Comparison of substituent effects on α‐, β‐, γ‐ and δ‐carbons in both series of compounds shows remarkable differences in steric interactions. In contrast to the rigid bicyclo[2.2.1]heptane system, both chair and boat conformations can be predominant in the bicyclo[3.2.1]octane series with the conformationally flexible 6‐membered ring.

Practical synthesis of brevicomin. V. Isomer enrichment of bicyclic ketals in the 6,8-dioxabicyclo[3.2.1]octane series by complexation with titanium tetrachloride

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTPractical synthesis of brevicomin. V. Isomer enrichment of bicyclic ketals in the 6,8-dioxabicyclo[3.2.1]octane series by complexation with titanium tetrachlorideKenneth B. Lipkowitz and Bradford P. MundyCite this: J. Org. Chem. 1976, 41, 2, 373Publication Date (Print):January 1, 1976Publication History Published online1 May 2002Published inissue 1 January 1976https://doi.org/10.1021/jo00864a042RIGHTS & PERMISSIONSArticle Views41Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (157 KB) Get e-Alerts Get e-Alerts

Investigation of the conformations of compounds of the trans-tricyclo[5,1,0,03.5]octane series

1. Polarity of 1,4-cyclohexadiene dioxide and its bis-adducts with dihalocarbenes was detected on the basis of an analysis of the electrooptical properties. 2. It was established by the method of dipole moments, Kerr constants, and depolarization of the Rayleigh light scattering of derivatives and analogs of bicyclo[5,1,0,03,5]octane that the cyclohexane ring, condensed with two three-membered rings, is nonplanar.

Calculs de conformation sur les systemes tendus.: Derives du bicyclo[3.2.1]octane hydrocarbure, cetone en −3 et derives bromes correspondants

We present the results of calculations according to the Westheimer-Hendrickson-Wiberg technique, on several derivatives in the bicyclo[3.2.1]octane series, the hydrocarbon, the 3-keto derivative and corresponding bromoketones. The method of calculation is essentially the one of our preceeding paper, but we have been using not only the same functions of interaction, but also others, for reasons which are discussed. We consider molecules which do not have a plane of symetry, a problem which has requested a more elaborated program. The different results are analyzed and compared. It is clearly shown that this kind of calculation is much more reliable from the geometric point of view, than it is on energetic grounds. The antireflex theory as well as its consequences are clearly shown. In all studied cases, the results of calculations have been compared to the experimental data.

Synthesis and investigation of the steric structure of certain compounds of the tricyclo [5,1,0,02,4]octane series

1. A number of adducts of dihalocarbenes with 1,3-cyclohexadiene and Δ4-carene were synthesized, and their dipole moments and molar Kerr constants were determined. 2. The addition of dihalocarbenes to bicyclo[4,1,0]-2-heptene proceeds with the formation of transtricyclooctanes. The conformation of the molecules of the investigated compounds was determined.

Free-radical addition reactions of some olefins related to bicyclo[2,2,2]octane

The products of the addition of benzenethiol to bicyclo[2,2,2]oct-2-ene, 2-methylenebicyclo[2,2,2]octane, 5-methylenebicyclo[2,2,2]oct-2-ene, 2,3-dimethylenebicyclo[2,2,2]octane, 5,6-dimethylenebicyclo[2,2,2]oct-2-ene, and 8,9-dimethylenebicyclo[3,2,2]non-6-ene have been investigated. The additions of methanethiol to 2,3-dimethylenebicyclo[2,2,2]octane, of p-thiocresol to 5,6-dimethylenebicyclo[2,2,2]oct-2-ene, and of bromotrichloromethane and methylene dibromide to bicyclo[2,2,2]oct-2-ene have also been studied. In the additions to mono-olefins, products of 1,2-addition to the double bond result, whereas with conjugated dienes products of 1,4-addition to the diene systems are formed. Only a few per cent, at most, of products of homoconjugative addition were isolated in the addition of benzenethiol to 5-methylenebicyclo[2,2,2]oct-2-ene. No such product was detected in additions to 5,6-dimethylenebicyclo[2,2,2]oct-2-ene and 8,9-dimethylenebicyclo[3,2,2]non-6-ene. The double bonds and diene systems in these compounds react independently of each other to a large extent. The reactivities (relative to oct-1-ene) of the olefins and dienes in the bicyclo[2,2,2]octane series towards benzenethiol, and towards methyl thioglycollate have been obtained. Apart from the conjugated dienes, which have high reactivities, the olefins and non-conjugated diene are less reactive than the corresponding compounds related to norbornene. This may indicate the smaller degree of strain in olefins in the bicyclo[2,2,2]octane series.

A revised structure for neogmelinol: determinations of configurations in tetrahydrofuranoid lignans

Neogmelinol is shown to be a stereoisomer rather than a structural isomer of gmelinol and isogmelinol, and its absolute configuration is established. A general criterion is established for assignment of stereochemistry in lignans of the 3,7-dioxabicyclo[3,3,0]octane series by the use of n.m.r. spectra. The relative stabilities of the isomers are discussed. The configuration of sesangolin is assigned.

Systems with Bridgehead Nitrogen. β-Ketols of the 1-Azabicyclo[2.2.2]octane Series

Systems with Bridgehead Nitrogen. β-Ketols of the 1-Azabicyclo[2.2.2]octane Series

PHOTOCHEMICAL SYNTHESES: 10. ADDITION OF MALEIC ESTER TO CYCLOALKENES: THE PRODUCTS

The intermolecular photochemical cycloaddition of maleic ester to cyclopentene and to cyclohexene has been observed. The saturated products were diesters of the (3:2:0) and (4:2:0) bicycloheptane and octane series, respectively. The stereochemistry of these products was studied and, in the latter series, derivatives of the trans-fused (4:2:0) bicyclooctane system identified.In addition to the saturated esters, cyclohex-2-enyl succinic ester and cyclopent-2-enyl succinic ester, produced by addition of the cycloalkenyl radical to maleic ester, also were formed.