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Diels-Alder Reactions of Tetradehydrodianthracene with Electron-Deficient Dienes

✍ Scribed by Sauer, Jürgen ;Breu, Josef ;Holland, Uwe ;Herges, Rainer ;Neumann, Helfried ;Kammermeier, Stefan

Publisher
John Wiley and Sons
Year
1997
Tongue
English
Weight
758 KB
Volume
1997
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

Theoretical calculations and simple MO considerations predict that a coplanar and spatially close arrangement of double bonds in structures such as tetradehydrodianthracene 1, should both lower the LUMO and raise the HOMO energy of the π system. Thus the reactivity in Diels‐Alder reactions towards electron‐rich, as well as electron‐deficient, dienes should be enhanced. The first effect has already been shown in a previous paper, the latter statement is now also confirmed by the reactivity of 1 in Diels‐Alder reactions with inverse electron demand. In [4 + 2] cycloaddition reactions of 1 with 1,2,4,5‐tetrazines 2 the electronic effect of 3,6 substituents in tetrazines is far outweighed by steric factors resulting in an unexpected reactivity sequence: 2a ≫ 2b ≈ 2c > 2d.

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