The University of Southampton
University of Southampton Institutional Repository

Bromine-lithium exchange on gem-dibromoalkenes Part 1: batch vs microflow conditions

Bromine-lithium exchange on gem-dibromoalkenes Part 1: batch vs microflow conditions
Bromine-lithium exchange on gem-dibromoalkenes Part 1: batch vs microflow conditions
The generation and reactivity of two model vinyl carbenoids from gem-dibromoalkenes 1 were studied in microflow systems. From substrate 1a (R = Ph, CF3), the lithium-bromine exchange could be simply performed within 30 ms at 20 °C with very good E-selectivity whereas the reaction was unselective under batch conditions, even at −78 °C. Moreover, the unstable carbenoid generated from 1b (R = Ph, H) could be trapped as the major product while only the Fritsch-Buttemberg-Wiechell rearrangement product was obtained in a flask under cryogenic conditions.
Fritsch-Buttemberg-Wiechell rearrangement, carbenoid, organolithium compounds, selectivity, microfluidics
2062-249X
139-143
Picard, Baptiste
7eb19b8c-ec0e-4338-93c9-b3feda00a06b
Perez, Katia
342362db-c394-4c54-aedd-df5f342bf1b8
Lebleu, Thomas
78571c1c-a9ea-4a45-b47e-cc76e2d0279d
Vuluga, Daniela
261e6c4f-f477-4829-b6df-1fb757f75553
Burel, Fabrice
4ddcd77b-b9dc-439e-ae9e-3ef1470eb821
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Chataigner, Isabelle
13a550db-1647-4178-8200-f2547b148729
Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa
Legros, Julien
0ad85dc7-e84f-4c8c-95a4-2aa46fbe89ec
Picard, Baptiste
7eb19b8c-ec0e-4338-93c9-b3feda00a06b
Perez, Katia
342362db-c394-4c54-aedd-df5f342bf1b8
Lebleu, Thomas
78571c1c-a9ea-4a45-b47e-cc76e2d0279d
Vuluga, Daniela
261e6c4f-f477-4829-b6df-1fb757f75553
Burel, Fabrice
4ddcd77b-b9dc-439e-ae9e-3ef1470eb821
Harrowven, David C.
bddcfab6-dbde-49df-aec2-42abbcf5d10b
Chataigner, Isabelle
13a550db-1647-4178-8200-f2547b148729
Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa
Legros, Julien
0ad85dc7-e84f-4c8c-95a4-2aa46fbe89ec

Picard, Baptiste, Perez, Katia, Lebleu, Thomas, Vuluga, Daniela, Burel, Fabrice, Harrowven, David C., Chataigner, Isabelle, Maddaluno, Jacques and Legros, Julien (2020) Bromine-lithium exchange on gem-dibromoalkenes Part 1: batch vs microflow conditions. Journal of Flow Chemistry, 10, 139-143. (doi:10.1007/s41981-019-00057-6).

Record type: Article

Abstract

The generation and reactivity of two model vinyl carbenoids from gem-dibromoalkenes 1 were studied in microflow systems. From substrate 1a (R = Ph, CF3), the lithium-bromine exchange could be simply performed within 30 ms at 20 °C with very good E-selectivity whereas the reaction was unselective under batch conditions, even at −78 °C. Moreover, the unstable carbenoid generated from 1b (R = Ph, H) could be trapped as the major product while only the Fritsch-Buttemberg-Wiechell rearrangement product was obtained in a flask under cryogenic conditions.

Text
Dibromo-Part1-MS-Rev - Accepted Manuscript
Restricted to Repository staff only until 14 February 2021.
Request a copy

More information

Accepted/In Press date: 11 November 2019
e-pub ahead of print date: 14 February 2020
Keywords: Fritsch-Buttemberg-Wiechell rearrangement, carbenoid, organolithium compounds, selectivity, microfluidics

Identifiers

Local EPrints ID: 435913
URI: http://eprints.soton.ac.uk/id/eprint/435913
ISSN: 2062-249X
PURE UUID: 947cb347-5b49-45e3-bddd-fb47b431874e
ORCID for David C. Harrowven: ORCID iD orcid.org/0000-0001-6730-3573

Catalogue record

Date deposited: 22 Nov 2019 17:30
Last modified: 16 May 2020 00:28

Export record

Altmetrics

Contributors

Author: Baptiste Picard
Author: Katia Perez
Author: Thomas Lebleu
Author: Daniela Vuluga
Author: Fabrice Burel
Author: Isabelle Chataigner
Author: Jacques Maddaluno
Author: Julien Legros

University divisions

Download statistics

Downloads from ePrints over the past year. Other digital versions may also be available to download e.g. from the publisher's website.

View more statistics

Atom RSS 1.0 RSS 2.0

Contact ePrints Soton: eprints@soton.ac.uk

ePrints Soton supports OAI 2.0 with a base URL of http://eprints.soton.ac.uk/cgi/oai2

This repository has been built using EPrints software, developed at the University of Southampton, but available to everyone to use.

We use cookies to ensure that we give you the best experience on our website. If you continue without changing your settings, we will assume that you are happy to receive cookies on the University of Southampton website.

×