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2005
Rings with 7 or more members
Q 0050
SO2-Extrusion of an 8-Thiabicyclo[3.2.1]octa-2,6-diene 8,8-Dioxide and Rearof the Resulting Cycloheptatriene. — Diels—Alder reaction of thio35- 075 rangement
phene oxide (I) with tetrachlorocyclopropene (II) furnishes the Diels—Alder adduct
with simultaneous chlorine migration to give adduct (III) as major product. Adduct (III)
is oxidized to sulfone (VI), the precursor of the desired cycloheptatriene. However,
thermolysis of (VI) does not yield the expected simple SO2-extrusion product but rearranged products (VII) and (VIII). In addition to SO2, the formation of (VII) requires the
elimination of HCl. Indeed, carrying out the thermolysis in the presence of a base to
promote elimination of HCl affords (VII) as the sole product. — (TAKAYAMA, J.;
SUGIHARA, Y.; NAKAYAMA*, J.; Heteroat. Chem. 16 (2005) 2, 132-137; Dep.
Chem., Fac. Sci., Saitama Univ., Urawa, Saitama 338, Japan; Eng.) —
H. Hoennerscheid
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