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3,5-Dimesityl-1,2,4-oxadiphosphole – Synthesis and Reactivity of a Novel Heterocycle

✍ Scribed by Andreas Mack; Uwe Bergsträßer; Guido J. Reiß; Manfred Regitz

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

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✦ Synopsis

The first synthesis of a 1,2,4-oxadiphosphole 6 has been cycloaddition with 12 and 13 leading to the spirocyclic products 15 and 16 containing λ 5 -phosphorus atoms. achieved by vacuum thermolysis of mesitylphosphaalkene 5. The novel heterocycle 6 exhibits an enormous potential for Treatment of the oxadiphosphole 6 with dimethyl acetylenedicarboxylate ( 17) provides the first access to a 1,2-cycloaddition reactions, which predominantly proceed selectively at low temperatures. Compound 6 undergoes oxaphosphole 18, which is formed after an initial [4+2] cycloaddition followed by a retro Diels-Alder reaction. An addition with two equivalents of phosphaalkynes 10 by a [4+2] cycloaddition/homo Diels-Alder reaction sequence to unexpected reaction of 6 is observed with tri-tert-butylazete (20) furnishing a new polycyclic system (Ǟ 21). form novel oxatetraphosphadeltacyclenes 12 and 13. Tetrachloro-o-benzoquinone ( 14) undergoes a selective [4+1] [ ] Part 137: Ref. [1] [a]

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