1‐Substituted 1,3‐Dihydroisothianaphthen‐2,2‐dioxides: Preparation and Use as  ortho ‐Quinodimethane Precursors in Intramolecular Cycloadditions. Preliminary communication | Zendy

Oppolzer Wofgang | Zendy; Roberts David A. | Zendy; Bird T. Geoffrey C. | Zendy

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1‐Substituted 1,3‐Dihydroisothianaphthen‐2,2‐dioxides: Preparation and Use as ortho ‐Quinodimethane Precursors in Intramolecular Cycloadditions. Preliminary communication

Author(s) -

Oppolzer Wofgang,

Roberts David A.,

Bird T. Geoffrey C.

Publication year - 1979

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19790620630

Subject(s) - chemistry , intramolecular force , deprotonation , electrophile , thermal decomposition , medicinal chemistry , extrusion , thioether , combinatorial chemistry , organic chemistry , ion , materials science , metallurgy , catalysis

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 SO 2 ‐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 ).

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