An unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment of aryl- and alkenyl-substituted allylic alcohols with activated isocyanates is reported. The reorganization of bonds is highly dependent on the electron density of the aromatic ring and the nature of isocyanate used. This metal-free tandem reaction from branched allyl alcohols initiated by a carbamoylation reaction and followed by a sigmatropic rearrangement thus offers a new access to (E)-cinnamyl and conjugated (E,E)-diene carbamates, such as N-acyl and N-sulfonyl derivatives. A computational study was conducted in order to rationalize this phenomenon, and a rearrangement progress kinetic analysis was performed
Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation result...
Enol carbamates (<i>O</i>-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and be...
Efficient, one-pot carbolithiation - alpha-alkylation and -[1.2]-Wittig rearrangement processes of a...
International audienceAn unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment o...
International audienceIn a first instance, the effect of the microwave irradiation on the 1,3-Dioxa-...
Nowadays, among all chemical transformations in the organic chemist’s toolbox, [3,3] sigmatropic rea...
De nos jours, parmi toutes les transformations chimiques dont disposent les chimistes organiciens, l...
International audience[3,3]-Sigmatropic rearrangements represent powerful methods in the toolbox of ...
International audienceThe combination of in situ generated α-isocyanato allylboronic esters and alde...
Retro-ene type [2π + 2π + 2σ] and [3,3]-sigmatropic shift reactions involving the substituent groups...
International audience[3,3]-Sigmatropic cyanate-isocyanate rearrangement provides a powerful tool fo...
Mechanisms of thermal isomerization of allyl tetrazolyl ethers derived from the carbocyclic allylic ...
A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rea...
The first (thio)cyanate to iso(thio)cyanate rearrangements based on 2-fluoroallylic alcohols are pre...
239 p.Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1985.A new variant of the Claisen ...
Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation result...
Enol carbamates (<i>O</i>-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and be...
Efficient, one-pot carbolithiation - alpha-alkylation and -[1.2]-Wittig rearrangement processes of a...
International audienceAn unexpected 1,3-dioxa-[3,3]-sigmatropic rearrangement during the treatment o...
International audienceIn a first instance, the effect of the microwave irradiation on the 1,3-Dioxa-...
Nowadays, among all chemical transformations in the organic chemist’s toolbox, [3,3] sigmatropic rea...
De nos jours, parmi toutes les transformations chimiques dont disposent les chimistes organiciens, l...
International audience[3,3]-Sigmatropic rearrangements represent powerful methods in the toolbox of ...
International audienceThe combination of in situ generated α-isocyanato allylboronic esters and alde...
Retro-ene type [2π + 2π + 2σ] and [3,3]-sigmatropic shift reactions involving the substituent groups...
International audience[3,3]-Sigmatropic cyanate-isocyanate rearrangement provides a powerful tool fo...
Mechanisms of thermal isomerization of allyl tetrazolyl ethers derived from the carbocyclic allylic ...
A gold-catalyzed [2,3]-sigmatropic rearrangement reaction has been developed. The intermolecular rea...
The first (thio)cyanate to iso(thio)cyanate rearrangements based on 2-fluoroallylic alcohols are pre...
239 p.Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1985.A new variant of the Claisen ...
Systematic evaluation of 1,5-dienes bearing 3,3-electron-withdrawing groups and 4-methylation result...
Enol carbamates (<i>O</i>-vinylcarbamates) derived from aromatic or α,β-unsaturated compounds and be...
Efficient, one-pot carbolithiation - alpha-alkylation and -[1.2]-Wittig rearrangement processes of a...