Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride
| dc.contributor.author | Weidkamp, Andreas J. | |
| dc.contributor.author | Oestreich, Martin | |
| dc.date.accessioned | 2022-04-11T06:38:55Z | |
| dc.date.available | 2022-04-11T06:38:55Z | |
| dc.date.issued | 2021-12-20 | |
| dc.description.abstract | The development and application of a transfer hydrochlorination reagent based on a trichlorinated bicyclo[3.1.0]hexane core that transfers two molecules of HCl per molecule of surrogate to a π-basic substrate under B(C6F5)3 catalysis is reported. Lewis acid-assisted chloride abstraction followed by thermal electrocyclic cyclopropyl-to-allyl cation ring opening releases ring strain as a previously unexploited driving force. | en |
| dc.description.sponsorship | TU Berlin, Open-Access-Mittel – 2021 | en |
| dc.identifier.eissn | 1364-548X | |
| dc.identifier.issn | 0022-4936 | |
| dc.identifier.uri | https://depositonce.tu-berlin.de/handle/11303/16695 | |
| dc.identifier.uri | http://dx.doi.org/10.14279/depositonce-15473 | |
| dc.language.iso | en | en |
| dc.rights.uri | https://creativecommons.org/licenses/by/3.0/ | en |
| dc.subject.ddc | 540 Chemie und zugeordnete Wissenschaften | de |
| dc.subject.other | C–C triple bonds | en |
| dc.subject.other | hydrogen chloride | en |
| dc.subject.other | hydrochlorination | en |
| dc.subject.other | transfer hydrochlorination reagent | en |
| dc.subject.other | trichlorinated bicyclo[3.1.0]hexane | en |
| dc.title | Metal-free transfer hydrochlorination of internal C–C triple bonds with a bicyclo[3.1.0]hexane-based surrogate releasing two molecules of hydrogen chloride | en |
| dc.type | Article | en |
| dc.type.version | publishedVersion | en |
| dcterms.bibliographicCitation.doi | 10.1039/D1CC06591B | en |
| dcterms.bibliographicCitation.issue | 7 | en |
| dcterms.bibliographicCitation.journaltitle | Chemical Communications | en |
| dcterms.bibliographicCitation.originalpublishername | Royal Society of Chemistry | en |
| dcterms.bibliographicCitation.originalpublisherplace | Cambridge | en |
| dcterms.bibliographicCitation.pageend | 976 | en |
| dcterms.bibliographicCitation.pagestart | 973 | en |
| dcterms.bibliographicCitation.volume | 58 | en |
| tub.accessrights.dnb | free | en |
| tub.affiliation | Fak. 2 Mathematik und Naturwissenschaften::Inst. Chemie::FG Organische Chemie / Synthese und Katalyse | de |
| tub.affiliation.faculty | Fak. 2 Mathematik und Naturwissenschaften | de |
| tub.affiliation.group | FG Organische Chemie / Synthese und Katalyse | de |
| tub.affiliation.institute | Inst. Chemie | de |
| tub.publisher.universityorinstitution | Technische Universität Berlin | en |