Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 1992; 1992(7): 581-584
DOI: 10.1055/s-1992-21423
DOI: 10.1055/s-1992-21423
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved.
This journal, including all individual contributions and illustrations published
therein, is legally protected by copyright for the duration of the copyright period.
Any use, exploitation or commercialization outside the narrow limits set by copyright
legislation, without the publisher's consent, is illegal and liable to criminal prosecution.
This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing
or duplication of any kind, translating, preparation of microfilms, and electronic
data processing and storage.Halosulphonylation of Unsaturated Boronic Esters: Access to New Electron-Deficient Alkenes and Dienes
Further Information
Publication History
Publication Date:
08 March 2002 (online)

Sulphonyl halides undergo free radical addition to vinyl- and 1,3-dienylboronic esters (2-vinyl-1,3,2-dioxaborolanes 1 and 2-(1,3-alkadienyl)-1,3,2-dioxaborolanes 5] giving adducts which, in appropriate cases, afford upon treatment with base new β-sulphonyl α,β-unsaturated boronic esters [2-(2-p-toluenesulphonylethenyl)-1,3,2-dioxaborolanes 3 and 2-(4-p-toluenesulphonyl-1,3-butadienyl)-1,3,2-dioxaborolanes 6, respectively]. By using bromomethanesulphonyl bromide, the parent 1,3-butadienyl-2-boronic ester 8 was synthesized via a vinylogous Ramberg-Bäcklund rearrangement of the corresponding β-bromosulphone 7.