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Domino [3+3] Annulation/Ring-Cleavage Reactions of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with 5-Aryl- and 5-Vinyl-3-acyl- 4,5-dihydrofurans: Efficient Synthesis of 5-(4-Chlorobut-2-en-1-yl)- and 5-(2-Aryl-2-chloroethyl)salicylates

✍ Scribed by Matthias Lau; Muhammad Sher; Alexander Villinger; Christine Fischer; Peter Langer

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
412 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

The domino “[3+3] cyclization–ring‐opening” reactions of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with 3‐acetyl‐5‐vinyl‐4,5‐dihydrofurans afforded 5‐(4‐halobut‐2‐en‐1‐yl)salicylates. The reactions of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with 3‐acetyl‐5‐aryl‐4,5‐dihydrofurans gave 5‐(2‐aryl‐2‐chloroethyl)salicylates.

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Synthesis of 9-Aryl-9,10-dihydrophenanth
Synthesis of 9-Aryl-9,10-dihydrophenanthrenes by Domino [3+3] Annulation/Ring-Opening/Friedel–Crafts Alkylation Reactions of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with 3-Aroyl-5-aryl-4,5-dihydrofurans
✍ Matthias Lau; Muhammad Sher; Alexander Villinger; Christine Fischer; Peter Lange 📂 Article 📅 2010 🏛 John Wiley and Sons 🌐 English ⚖ 420 KB

## Abstract The reaction of 1,3‐bis(trimethylsilyloxy)‐1,3‐butadienes with 3‐benzoyl‐5‐aryl‐4,5‐dihydrofurans, available by CAN‐mediated reaction of styrenes with benzoylacetones, afforded functionalized 9,10‐dihydrophenanthrenes. These reactions proceed by a novel domino [3+3] cyclization/ring‐ope