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Easy and Regioselective Synthesis of Highly Functionalized o-Quinodimethide Precursors from Fischer Carbene Complexes and Isocyanides

✍ Scribed by José Barluenga; Fernando Aznar; M. Angel Palomero


Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
300 KB
Volume
8
Category
Article
ISSN
0947-6539

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✦ Synopsis


Highly functionalized cis- and trans-1,2-bis(trialkylsilyloxy)benzocyclobutene derivatives have been synthesized in a completely regioselective fashion from easily available Fischer alkenylcyclobutenyl(alkoxy)carbene complexes and isocyanides. This methodology can be viewed as an alternative to existing methods of synthesis of this kind of compounds and overcomes the main problem of introducing functionality in the aromatic ring. Both cis and trans derivatives underwent the expected fragmentation to generate o-quinodimethide intermediates upon thermal treatment, affording complex polycyclic structures in a stereoselective manner when heating was carried out in the presence of a range of electron deficient dienophiles.


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✍ José Barluenga; Fernando Aznar; M. Angel Palomero 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 132 KB 👁 1 views

A range of stable chromium and tungsten Fischer dienyl carbenes have been prepared by [3+2] cycloaddition of alkenylethynyl carbene complexes with nitrones or diazoalkanes. Treatment of these systems with isocyanides gives entry to highly functionalized 2,3-dihydro-1,2-benzisoxazoles and indazoles i