Abstract
The title tetrone compound, C32H22N2O4S· 0.5C8H10, is the major product (50% yield) of an attempted Diels-Alder reaction of 2-(α-styr-yl)thio-phene with N-phenyl-male-imide (2 equivalents) in toluene. Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene mol-ecule is located about an inversion center. In the crystal, the primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bi-cyclo-[2.2.2]octene core, forming chains along [001].
Highlights
Recrystallization of the resulting powder from p-xylene gave the title hemisolvate; the p-xylene molecule is located about an inversion center
The primary tetrone contacts are between a carbonyl O atom and the four flagpole H atoms of the bicyclo[2.2.2]octene core, forming chains along [001]
The title compound, (3), is the first reported double-Diels–Alder adduct obtained from a one-pot reaction of a 2-vinylthiophene (Fig. 1)
Summary
Alder adduct obtained from a one-pot reaction of a 2-vinylthiophene (Fig. 1). This methodology may have use in the synthesis of novel ligands, zeolites, or polyamides. Diels–Alder methodology: Reactions between vinylheterocycles and dienophiles have been useful in natural product synthesis and in the development of potential medicinal compounds (Booth et al, 2005; Kanai et al, 2005). Brewer & Elix (1975a) reported a double adduct (10) and a hydroperoxy intermediate thereof; they proposed loss of H2 in an autoxidation followed by elimination of H2O2, a pathway that fits both observations made by the Noland group.
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Free) 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
