53. 1-Substituted 1,3-Dihydroisothianaphthen-2,2-dioxides: Preparation and Use as ortho-Quinodimethane Precursors in Intramolecular Cycloadditions. Preliminary communication
    Oppolzer, W.; Roberts, D. A.; Bird, T. G. C.
    Helv. Chim. Acta 1979, 62, 2017-2021

1,3-Dihydroisothianaphthen-2,2-dioxide (1) was readily converted to the 1-substituted sulfones 3 by deprotonation and subsequent electrophilic attack (Scheme 3 and Table). The appropriate 1-alkenyl- and 1-alkenoyl-sulfones 3 on heating at 213° to 240° underwent SO₂-extrusion to give, via the non-isolated (E)-quinodimethanes II (Scheme 1), polycyclic products such as 4, 6 and 7 in good yields (Schemes 4 and 5). On the other hand, thermolysis of the 1-alkenoyl-1-thioether sulfones 9 furnished mainly the isochromenes 10 (Scheme 6).

DOI : 10.1002/hlca.19790620630