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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 ).