Synthesis of new tricyclic phosphines and phosphinites by intramolecular Diels-Alder reactions of trivalent phospholes.
Phospholes bearing an allyl-X substituent at phosphorus tend to undergo an intramolecular Diels-Alder cycloaddition (IMDA) leading to the corresponding tricyclic derivative. When X = O or NR, the IMDA easily takes place at room temperature. When X = CH2, the IMDA slowly takes place around 110-140 degrees C, as a function to the substitution pattern of the dienic system. Two tricyclic derivatives (X = O and CH2) have been characterized by X-ray crystal structure analysis of the P-sulfides.
Laboratoire "Hétéroéléments et Coordination" UMR CNRS 7653, DCPH, Ecole Polytechnique, 91128 Palaiseau Cedex, France.
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Mattmann
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Mercier
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Ricard
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Mathey