One-pot thermally chemocontrolled double Diels-Alder strategies. A route to [4+2] functionalisation/[4+2] derivatization of C-60 (Journal article)
Markoulides, M. S./ Ioannou, G. I./ Manos, M. J./ Chronakis, N.
The one-pot double Diels-Alder reactions of 3,4-di(methylene)tetrahydrothiophene-1,1-dioxide using temperature as the only chemocontrol element are described. Zn-dust promoted the 1,4-debromination of 3,4-bis(bromomethyl)-2,5-dihydrothiophene-1,1-dioxide in 5-nonanone, under MW conditions, followed by a Diels-Alder reaction, an SO2 extrusion step and a second Diels-Alder reaction. This approach was applied successfully in double [4 + 2] cycloadditions using the same or two different dienophiles to afford the corresponding Diels-Alder products in excellent yields. An elegant and practical method for [4 + 2] functionalisation/[4 + 2] derivatization of C-60 was achieved in a one-pot manner via the formation of a new reactive C-66 dienic intermediate.
|Institution and School/Department of submitter:||Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας|
|Keywords:||efficient preparation,electron-transfer,fullerene c-60,pi-donors,chemistry,rongalite,derivatives,anthracene,expansion,adducts|
|Link:||<Go to ISI>://000315905400040|
|Publisher:||Royal Society of Chemistry|
|Appears in Collections:||Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)|
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