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Addition of silyloxydienes to 2-substituted 1,4-benzoquinones and 1,4-naphthoquinones

โœ Scribed by Margaret A Brimble; Richard J.R Elliott

Publisher
Elsevier Science
Year
1997
Tongue
French
Weight
869 KB
Volume
53
Category
Article
ISSN
0040-4020

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โœฆ Synopsis

afforded Diels-Alder adduct 14 and fragmentation product 32 with 2 and 3 respectively whereby reaction occurred on the less substituted double bond. No adducts were isolated upon treatment of naphthoquinone-sulfide 22 with either 2 or 3. The Diels-Alder adducts of benzoquinone-sulfoxide 9 and naphthoquinone-sulfoxide 23 with 2 underwent facile aromatisation to 1,4-naphthoquinone and 9,10anthracenedione with 2. Addition of 3 to 9 afforded fragmentation product 33 whereas analogous reaction with 23 was unsucccessful. Addition of dienes 2,3 to benzoquinone-sulfone 10 afforded fragmentation products 16,34 respectively, whereas naphthoquinone-sulfone 24 afforded 9,10anthracendione with 2 and no products with 3.

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