76570-82-6Relevant academic research and scientific papers
New Cyclisation Reaction of Aryl-lithium Species; X-Ray Crystal Structure of (2,3-dihydro-3-benzofuryl)acetanilide
Baldwin, J. E.,Dupont, W. A.,Ming, M. F.
, p. 1042 - 1043 (1980)
Direct metallation of 3-allyloxybenzanilides gave the 2-lithioderivatives, which underwent a cyclisation process to yield (2,3-dihydrobenzofuryl)acetanilides; the structure of (2,3-dihydro-3-benzofuryl)acetanilide has been determined by X-ray crystallogra
Intramolecular carbolithiation of allyl o-lithioaryl ethers: A new enantioselective synthesis of functionalized 2,3-dihydrobenzofurans
Barluenga, Jose,Fananas, Francisco J.,Sanz, Roberto,Marcos, Cesar
, p. 5397 - 5407 (2007/10/03)
A new and easy method for the diastereoselective synthesis of 3-functionalized 2,3-dihydrobenzofuran derivatives from allyl 2-bromoaryl ethers is described. The key step of this transformation involves an intramolecular carbolithiation reaction of allyl 2-lithioaryl ethers. The substituents in both the allyl and the aryl moieties play an important and decisive role in stopping the reaction at the benzofuran thus avoiding a γ-elimination reaction. Finally, this process is amenable to the synthesis of enantiomerically enriched compounds by using ( - )-sparteine as a chiral inductor.
The samarium grignard reaction. In situ formation and reactions of primary and secondary alkylsamarium(III) reagents
Curran, Dennis P.,Totleben, Michael J.
, p. 6050 - 6058 (2007/10/02)
This work shows that primary and secondary radicals are rapidly reduced in THF/HMPA to form primary- and secondary-alkylsamarium reagents. The primary- and secondary-radicals can be formed either by direct SmI2 reduction of primary- and secondary-halides or by a previous rapid radical cyclization. The samarium reagents have moderate stability in solution, and they react with a variety of typical electrophiles, including aldehydes and ketones. The work further shows that organosamarium intermediates can be involved in the traditional samarium Barbier reaction of aldehydes and ketones conducted in THF/HMPA. A new procedure called the "samarium Grignard" method is introduced, and it is suggested that this new procedure will have considerably more scope and generality than the samarium Barbier reaction.
