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On the Behavior of 5,8-Bis(trimethylsilyl)cycloocta-1,3,6-triene in Cycloaddition Reactions and Subsequent Chemistry

✍ Scribed by Michael A. Hofmann; Anja Nachbauer; Uwe Bergsträßer; Manfred Regitz

Publisher
John Wiley and Sons
Year
1999
Tongue
English
Weight
361 KB
Volume
1999
Category
Article
ISSN
1434-193X

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✦ Synopsis

Phosphaalkynes 2 and electron-deficient alkynes 11 readily configuration of the phophatricyclodecadienes 12. In solution the tricyclodecadienes 13 are prone to facile cycloreversion react in a [4 + 2] cycloaddition process with 5,8bis(trimethylsilyl)cycloocta-1,3,6-triene (8) in its bicyclic form yielding the phthalic esters 15 and the cyclobutene 16. The latter is rapidly converted into the corresponding 1,3-10 to furnish regioselectively the tricyclodecadienes 12 and 13, respectively. The phosphorus-containing compounds 12 butadiene 18, which can be trapped in a Diels-Alder/ phospha-ene/Diels-Alder tandem reaction sequence by exhibit structural features which make them suitable for homo-Diels-Alder reactions with electron-deficient phosphaalkyne 2a. The phosphatricyclodecadiene 12 is thermally more stable; loss of cyclobutene 16 only occurs acetylenes. A single crystal structure analysis of the homo-Diels-Alder adduct 14b confirmed the structure and relative under FVP conditions to afford the λ 3 -phosphinine 22.

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