Unexpected Migration and O to S Benzylic Shift of Thiocarbamate‐containing Salicylaldehyde Derivatives. | Zendy

Mangue Jordan | Zendy; Dubreucq Quentin | Zendy; Pécaut Jacques | Zendy; Ménage Stéphane | Zendy; Torelli Stéphane | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Premium

Unexpected Migration and O to S Benzylic Shift of Thiocarbamate‐containing Salicylaldehyde Derivatives.

Author(s) -

Mangue Jordan,

Dubreucq Quentin,

Pécaut Jacques,

Ménage Stéphane,

Torelli Stéphane

Publication year - 2016

Publication title -

chemistryselect

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.437

H-Index - 34

ISSN - 2365-6549

DOI - 10.1002/slct.201601374

Subject(s) - thiocarbamate , chemistry , aldehyde , thiocarbamates , steric effects , reactivity (psychology) , salicylaldehyde , ring (chemistry) , aryl , medicinal chemistry , organic chemistry , stereochemistry , catalysis , medicine , schiff base , alternative medicine , alkyl , pathology

Abstract : An unexpected reactivity of the O ‐dimethylthiocarbamate function has been evidenced concomitantly with the reduction of an aldehyde function presents at its ortho (o‐) position. A systematic study using various substrates showed the exclusive formation of the rearranged compounds after 24 h and confirmed that the only‐reduced compounds are reaction intermediates. However, electronic/steric contributions of the aromatic ring substituents on the composition of the reaction mixture (reduction of the aldehyde vs . migration) were observed at the early stage of the reaction (2 h). These new benzyl S ‐thiocarbamates compounds could be of particular interest as precursors for not trivial and functionalized free methylthiobenzyl alcohols.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research