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Copper (II) as catalyst for intramolecular cyclization and oxidation of (1,4-phenylene)bisguanidines to benzodiimidazole-diylidenes

dc.contributor.authorMesias-Salazar A.
dc.contributor.authorTrofymchuk O.S.
dc.contributor.authorDaniliuc C.G.
dc.contributor.authorAntiñolo A.
dc.contributor.authorCarrillo-Hermosilla F.
dc.contributor.authorNachtigall F.M.
dc.contributor.authorSantos L.S.
dc.contributor.authorRojas R.S.
dc.date.accessioned2020-09-02T22:22:59Z
dc.date.available2020-09-02T22:22:59Z
dc.date.issued2020
dc.identifier10.1016/j.jcat.2019.12.002
dc.identifier.citation382, , 150-154
dc.identifier.issn00219517
dc.identifier.urihttps://hdl.handle.net/20.500.12728/5327
dc.descriptionA synthetically useful approach of catalytic intramolecular cyclization and oxidation of 2′,2′-(1,4-phenylene)bis(1,3-dialkyl)guanidines (Alkyl = isopropyl 1 or cyclohexyl 2) catalyzed by copper acetate in acetonitrile under air was studied by on line monitoring of the reaction by ESI-MS. All-important intermediates organic species were intercepted during the experiment confirming for the first time the stepwise (1,4-phenylene)bisguanidines cyclization and oxidation mechanism. Moreover, performed collision-induced dissociation (CID) experiments were also applied as a structure elucidation tool. Bimetallic copper intermediates Cu1 ([C28H48Cu2N6O10 + H]+) of m/z 755 and Cu2 [C22H36Cu2N6O4 + H]+ of m/z 575 were documented. The plausible key mechanistic steps involving the formation of organic and inorganic intermediates detected by in situ monitoring of the reaction are presented. © 2019 Elsevier Inc.
dc.language.isoen
dc.publisherAcademic Press Inc.
dc.subjectCatalysis
dc.subjectCopper acetate
dc.subjectCyclization
dc.subjectESI-MS
dc.subjectGuanidines
dc.subjectCatalysis
dc.subjectCatalytic oxidation
dc.subjectCopper compounds
dc.subjectOxidation
dc.subjectReaction intermediates
dc.subjectCollision induced dissociation
dc.subjectCopper acetates
dc.subjectESI-MS
dc.subjectGuanidines
dc.subjectIn- situ monitoring
dc.subjectIntramolecular cyclizations
dc.subjectOxidation mechanisms
dc.subjectStructure elucidation
dc.subjectCyclization
dc.titleCopper (II) as catalyst for intramolecular cyclization and oxidation of (1,4-phenylene)bisguanidines to benzodiimidazole-diylidenes
dc.typeArticle


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