Advanced search
Start date
Betweenand
Related content
(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Unusual mechanisms in Claisen rearrangements: an ionic fragmentation leading to a meta-selective rearrangement

Full text
Author(s):
Show less -
Maryasin, Boris [1, 2] ; Kaldre, Dainis [2] ; Galaverna, Renan [3] ; Klose, Immo [2] ; Ruider, Stefan [1, 2] ; Drescher, Martina [2] ; Kaehlig, Hanspeter [2] ; Gonzalez, Leticia [1] ; Eberlin, Marcos N. [3] ; Jurberg, Igor D. [4] ; Maulide, Nuno [2]
Total Authors: 11
Affiliation:
[1] Univ Vienna, Inst Theoret Chem, Fac Chem, Wahringer Str 17, A-1090 Vienna - Austria
[2] Univ Vienna, Inst Organ Chem, Fac Chem, Wahringer Str 38, A-1090 Vienna - Austria
[3] Univ Estadual Campinas, Inst Chem, ThoMSon Mass Spectrometry Lab, Rua Monteiro Lobato 270, BR-13083970 Campinas, SP - Brazil
[4] Univ Estadual Campinas, Inst Chem, Rua Monteiro Lobato 270, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 4
Document type: Journal article
Source: CHEMICAL SCIENCE; v. 9, n. 17, p. 4124-4131, MAY 7 2018.
Web of Science Citations: 11
Abstract

A mechanistic investigation of the acid-catalysed redox-neutral oxoarylation reaction of ynamides using electrospray ionisation mass-spectrometry (ESI-MS) and quantum chemical calculations (DFT and MP2) is presented. This study reveals the diversity of pathways and products available from an otherwise deceptively simple-looking, classical transformation: fragmentation, an unusual meta-arylation and competing alpha-carbonyl cation pathways are some of the alternatives unveiled by ESI-MS and mechanistic experiments. Detailed calculations explain the observed trends and rationalise the results. (AU)

FAPESP's process: 15/20809-4 - Exploring the Chemistry of Isoxazol-5-ones as Versatile Building Blocks in Organic Synthesis
Grantee:Igor Dias Jurberg
Support Opportunities: Regular Research Grants