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
URI: http://olympias.lib.uoi.gr/jspui/handle/123456789/8687
ISSN: 2046-2069
Link: <Go to ISI>://000315905400040
http://pubs.rsc.org/en/Content/ArticleLanding/2013/RA/c3ra23327h
Publisher: Royal Society of Chemistry
Appears in Collections:Άρθρα σε επιστημονικά περιοδικά ( Ανοικτά)

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