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2-Hydroxybenzocyclobutenone Ethylene Dithioacetals as Precursors of Highly Substituted 1,4-Dihydronaphthalenes

✍ Scribed by Konstantin Benda; Wilko Regenhardt; Ernst Schaumann; Gunadi Adiwidjaja

Publisher
John Wiley and Sons
Year
2009
Tongue
English
Weight
259 KB
Volume
2009
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

1,4‐Dihydronaphthalenes 2, 9, and 11 with a spiro‐connected 1,3‐dithiolane ring as well as tetrahydronaphthalenes 15, 17, and 19 have been obtained from o‐quinodimethanes 3 and alkynes 4, naphthoquinones 10, or alkenes 14 and 16. Benzocyclobutenol 6 is not an appropriate quinodimethane precursor as it readily rearranges to phthalaldehyde derivative 7. However, silyl ether 8, silyl ether 13, obtained by the hydrosilylation of cyclobutenol 5, or aluminium alkoxide 3d, generated in situ by DIBAL reduction of 5, are useful sources of the corresponding quinodimethanes. The use of 3b,c gives a reversal of regioselectivity compared with 3d in the cycloaddition with propriolate 4a (product 9a vs. 2a). Naphthoquinone 10 reacts in the cycloaddition with 3b,c through its C2=C3 bond or through a C=O unit to give 11 and 12. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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