Cleavage Of Cyclopropane Ring Research Articles

Mechanism of hydrogen transfer in the reduction of the imine bond by an NADH model. Use of cyclopropane ring as a chemical probe

Reduction of N-cyclopropylmethylenephenylamine by 3,5-diethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine (Hantzsch ester) results in the exclusive formation of N-cyclopropylmethylaniline, whereas reduction with triphenyltin hydride gives both N-cyclopropylmethylaniline and n-butylaniline, a product of cyclopropane ring cleavage.

Nucleophilic and acid-catalyzed cleavage of the cyclopropane rings of β,γ-unsaturated α-spirocyclopropyl ketones

Treatment of isophorone (8) with sodium amide and 1,2-dibromomethane gives 6,6-dimethyl-8-methylenespiro[2.5]octan-4-one (9) and 6,6,8-trimethylspiro[2.5]oct-7-en-4-one (10); similar treatment of 3-methylcyclohex-2-en-1-one (5) gives analogous spiro compounds 6 and 7 together with 8-methylenedispiro[2.1.2.3]decan-4-one (11) and 8-methyldispiro[2.1.2.3]dec-8-en-4-one (12). The spiro ketones 6, 7, 9, and 10 undergo homoconjugate nucleophilic addition on being heated in morpholine with cleavage of the cyclopropane rings to give 2-[2-(4-morpholinyl)ethyl]cyclohex-2-en-1-ones. The rates of reaction are much greater for the exo methylene compounds 6 and 9 than for their endo isomers 7 and 10, but the rate of reaction of 10 is only slightly greater than that of the corresponding saturated compound, 6,6,8-trimethylspiro[2.5]octan-4-one (15). A corresponding rate differential between 9 and 10 is observed in their reactions with isophorone (8) and sodium hydride to give 2,2′-(ethanediyl)bis[3,5,5-trimethylcyclohex-2-en-1-one] (18). The acceleration in the cases of 6 and 9 relative to that of 15 is attributed to spiroactivation by both the carbonyl and exocyclic ethylenic groups; the much smaller effect of the endocyclic ethylenic groups in the cases of 7 and 10 is ascribed to torsional strain in the transition states for ring opening. The spiro ketones 6, 7, 9, and 10 also undergo acid-catalyzed cyclopropane ring cleavage in ethanol, giving 2-(2-ethoxyethyl)cyclohex-2-en-1-ones. Again the exo methylene compounds 6 and 9 react much more rapidly than their endo isomers 7 and 10; this is considered to be due to factors analogous to those operative in the nucleophilic addition reactions and/or the more rapid protonation of the exo methylene compounds.

ChemInform Abstract: CYCLOPROPANE RING CLEAVAGE IN THE α‐SANTAL SERIES. I. ABSOLUTE CONFIGURATIONS OF (‐)‐β‐SANTALOL, (+)‐EPI‐β‐SANTALOL, AND (E)‐(‐)‐β‐SANTALOL

Chemischer InformationsdienstVolume 13, Issue 40 Natural Products ChemInform Abstract: CYCLOPROPANE RING CLEAVAGE IN THE α-SANTAL SERIES. I. ABSOLUTE CONFIGURATIONS OF (-)-β-SANTALOL, (+)-EPI-β-SANTALOL, AND (E)-(-)-β-SANTALOL E.-J. BRUNKE, E.-J. BRUNKESearch for more papers by this authorA. + BOEHME, A. + BOEHMESearch for more papers by this authorH. STRUWE, H. STRUWESearch for more papers by this author E.-J. BRUNKE, E.-J. BRUNKESearch for more papers by this authorA. + BOEHME, A. + BOEHMESearch for more papers by this authorH. STRUWE, H. STRUWESearch for more papers by this author First published: October 5, 1982 https://doi.org/10.1002/chin.198240332Read 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. Volume13, Issue40October 5, 1982 RelatedInformation

Electrophilic cleavage of cyclopropanes. The areneselenenylation of tetracyclo[3.2.0.02,7.04,6]heptane (quadricyclene)1,2

The reaction of benzeneselenenyl chloride with tetracyclo[3.2.0.02,7.04,6]heptane (quadricyclene) yields, under conditions of kinetic control, adducts of both 1,3- and conjugative 1,6-addition, the latter being formed preferentially. Electrophilic cleavage of the cyclopropane ring occurs by both retention and inversion of configuration. In agreement with the known propensity for bond cleavage in this system only the C5—C6 and/or the C1—C7 bonds are broken. The rate of cyclopropane ring cleavage is found to follow second order kinetics, first order in quadricyclene and first order in selenenyl chloride; kobs = 1850 vs. 12 300 dm3 mol−1 s−1 for bicyclo[2.2.1]hepta-2,5- diene at 24.5 °C in methylene chloride solvent. The use of nucleophilic solvents such as HOAc, CH3OH, and CH3CN gives products of solvent-incorporation, preferentially via 1,3-addition.

Studies in sesquiterpenes—LVI: Isolongifolene (part 7) : mechanism of rearrangement of longifolene to isolongifolene—II

The question of possible neutral intermediates which may lie on the reaction pathway in going from longifolene to isolongifolene has been investigated using BF 3·Et 2O-AcOD and D 3PO 4-dioxane, as reagents. It has been found that longicyclene is not an obligatory intermediate. The mode of cleavage of cyclopropane ring in longicyclene has been investigated.

Novel Lactonization of γ-Cyclopropyl Carboxylic Acid via Acid-catalyzed Cleavage of Cyclopropane Ring

Abstract 4,6,10,l0-Tetramethyltricyclo[4.4.0.01,3undec-4-ene-5-carboxylic acid has been converted to a tricyclic γ-butyrolactone by perchloric acid catalyzed isomerization. Acetalization of the ketocarboxylic acid afforded an acetal derivative of γ-butyrolactone.

ChemInform Abstract: CYCLOPROPANE RING CLEAVAGE IN 3α,5‐CYCLO STEROID HYDROCARBONS

Chemischer InformationsdienstVolume 10, Issue 30 Natural Products ChemInform Abstract: CYCLOPROPANE RING CLEAVAGE IN 3α,5-CYCLO STEROID HYDROCARBONS E.-J. BRUNKE, E.-J. BRUNKESearch for more papers by this author E.-J. BRUNKE, E.-J. BRUNKESearch for more papers by this author First published: July 24, 1979 https://doi.org/10.1002/chin.197930357Read 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 onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume10, Issue30July 24, 1979 RelatedInformation

ChemInform Abstract: CLEAVAGE OF CYCLOPROPANE RINGS WITH RHODIUM(I) OCTAETHYLPORPHYRIN ANION

Chemischer InformationsdienstVolume 6, Issue 41 Organoelement Compounds ChemInform Abstract: CLEAVAGE OF CYCLOPROPANE RINGS WITH RHODIUM(I) OCTAETHYLPORPHYRIN ANION H. OGOSHI, H. OGOSHISearch for more papers by this authorJ. SETSUNE, J. SETSUNESearch for more papers by this authorZ. YOSHIDA, Z. YOSHIDASearch for more papers by this author H. OGOSHI, H. OGOSHISearch for more papers by this authorJ. SETSUNE, J. SETSUNESearch for more papers by this authorZ. YOSHIDA, Z. YOSHIDASearch for more papers by this author First published: October 14, 1975 https://doi.org/10.1002/chin.197541370Read 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 onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume6, Issue41October 14, 1975 RelatedInformation

Stereochemistry and mechanism of ionic cyclopropane ring cleavage by arenesulfenyl chloride addenda in quadricyclene systems

Stereochemistry and mechanism of ionic cyclopropane ring cleavage by arenesulfenyl chloride addenda in quadricyclene systems

ChemInform Abstract: SYNTHESIS OF SOME 4‐SUBSTITUTED PENTACYCLO(4.3.0.0(2,4).0(3,8).0(5,7))NONANE DERIVATIVES AND THEIR REACTIONS, CYCLOPROPANE RING EXPANSION AND CLEAVAGE

Chemischer InformationsdienstVolume 6, Issue 29 Isocyclic Compounds ChemInform Abstract: SYNTHESIS OF SOME 4-SUBSTITUTED PENTACYCLO(4.3.0.0(2,4).0(3,8).0(5,7))NONANE DERIVATIVES AND THEIR REACTIONS, CYCLOPROPANE RING EXPANSION AND CLEAVAGE T. SASAKI, T. SASAKISearch for more papers by this authorS. EGUCHI, S. EGUCHISearch for more papers by this authorF. HIBI, F. HIBISearch for more papers by this authorO. HIROAKI, O. HIROAKISearch for more papers by this author T. SASAKI, T. SASAKISearch for more papers by this authorS. EGUCHI, S. EGUCHISearch for more papers by this authorF. HIBI, F. HIBISearch for more papers by this authorO. HIROAKI, O. HIROAKISearch for more papers by this author First published: July 22, 1975 https://doi.org/10.1002/chin.197529225AboutPDF 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. Volume6, Issue29July 22, 1975 RelatedInformation

Synthesis of some 4-substituted pentacyclo[4.3.0.02,403,805,7]nonane derivatives and their reactions. Cyclopropane ring expansion and cleavage

Synthesis of some 4-substituted pentacyclo[4.3.0.02,403,805,7]nonane derivatives and their reactions. Cyclopropane ring expansion and cleavage

Cleavage of cyclopropane rings with rhodium(I) octaethylporphyrin anion

Reactions of rhodium(I) octaethylporphyrin ion with cyclopropanes substituted with an electron-with-drawing group and with highly strained cyclopropane derivatives such as quadricyclane gave alkylrhodium(III) octaethylporphyrin complexes resulting from C–C bond cleavage of the cyclopropane ring.

ChemInform Abstract: STEREOCHEMISTRY AND REACTIVITY IN CYCLOPROPANE RING‐CLEAVAGE BY ELECTROPHILES

Chemischer InformationsdienstVolume 4, Issue 49 Isocyclic Compounds ChemInform Abstract: STEREOCHEMISTRY AND REACTIVITY IN CYCLOPROPANE RING-CLEAVAGE BY ELECTROPHILES C. H. DEPUY, C. H. DEPUYSearch for more papers by this author C. H. DEPUY, C. H. DEPUYSearch for more papers by this author First published: December 4, 1973 https://doi.org/10.1002/chin.197349234Read 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. Volume4, Issue49December 4, 1973 RelatedInformation

Bridged polycyclic compounds. LXXI. Stereochemistry and mechanisms of cyclopropane ring cleavage. Addition of hydrogen chloride to tetracyclo[3.2.0.02,7.04,6]heptane-1,5-dicarboxylic acid (quadricyclenedicarboxylic acid)

Bridged polycyclic compounds. LXXI. Stereochemistry and mechanisms of cyclopropane ring cleavage. Addition of hydrogen chloride to tetracyclo[3.2.0.02,7.04,6]heptane-1,5-dicarboxylic acid (quadricyclenedicarboxylic acid)

Reactions of bicyclo[2.1.0]pentane and bicyclo[4.1.0]heptane with hydrogen chloride. Cleavage of cyclopropane rings

Reactions of bicyclo[2.1.0]pentane and bicyclo[4.1.0]heptane with hydrogen chloride. Cleavage of cyclopropane rings

Cyclopropanes. XXX. Reductive cleavage of cyclopropane rings

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTCyclopropanes. XXX. Reductive cleavage of cyclopropane ringsHarry M. Walborsky, M. S. Aronoff, and M. F. SchulmanCite this: J. Org. Chem. 1971, 36, 8, 1036–1040Publication Date (Print):April 1, 1971Publication History Published online1 May 2002Published inissue 1 April 1971https://doi.org/10.1021/jo00807a004RIGHTS & PERMISSIONSArticle Views326Altmetric-Citations16LEARN 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 (769 KB) Get e-Alerts Get e-Alerts

Mechanism of Cyclopropane Ring Cleavage in Cyclopropanecarboxylic Acid

Abstract Cells of Fusarium oxysporum Schlectendahl can convert cyclopropanecarboxylic acid to γ-hydroxybutyric acid. The first step in this degradative pathway is the derivatization of cyclopropanecarboxylate to a compound that contains the intact cyclopropylcarbonyl moiety. This paper demonstrates that the most probable second step in this pathway is the opening of the cyclopropane ring by the direct addition of water across one of its carbon to carbon single bonds.

Cyclopropanes. XXV. Cleavage of cyclopropane rings by solutions of sodium in liquid ammonia

Cyclopropanes. XXV. Cleavage of cyclopropane rings by solutions of sodium in liquid ammonia

Acid-catalyzed hydrolysis of 1-arylcylclopropyl acetates; electrophilic cyclopropane ring cleavage

Acid-catalyzed hydrolysis of 1-arylcylclopropyl acetates; electrophilic cyclopropane ring cleavage

Cyclopropane ring cleavage with n-bromosuccinimide

Cyclopropane ring cleavage with n-bromosuccinimide