Diels–Alder reactions involving CP– functionality

Asymmetric Diels–Alder reaction with >C=P– functionality of the 2-phosphaindolizine-η1-P-aluminium(O-menthoxy) dichloride complex: experimental and theoretical results

“…The first DA reaction involving the –C=C–C=P– moiety of phosphinine as a diene was reported by Märkl and Lieb [14], while Mathey and Alcaraz showed that phosphinine could react as a dienophile as well, with the reaction taking place at the >C=P– functionality of phosphinine [15]. We recently compiled a review on the DA reactions involving the >C=P– functionality of various organophosphorus compounds wherein all these aspects have been discussed [16]. …”

“…During the past few years, we have investigated the DA reaction with the >C=P – functionality of 1,3-azaphospholes theoretically as well as experimentally [16]. In this context, we found that 1,3-bis(alkoxycarbonyl)-2-phosphaindolizines ( 1a , Z = CO 2 R 1 ) prepared through 1,5-electrocyclization of in situ generated bis(pyridinium ylidyl)phosphenium chlorides [17] lead to successful DA reaction [18–19], but 3-alkoxycarbonyl-2-phosphaindolizines having an electron-withdrawing group (EWG) only at the 3-position ( 1b , Z = Me) failed to undergo DA reaction even on heating under reflux in toluene alone or in the presence of sulfur [18] (Scheme 1).…”

Phosphines and related C–P bonded compounds

“…349 The behaviour of the CQP functionality of phosphaalkenes and related heterocyclic systems in Diels-Alder reactions has been reviewed. 350 Phosphaalkenes have been introduced as long-lived phosphorus cluster surface functional groups to a niobium-supported P 7 cage structure. 351 The configurational and conformational properties of the various stereoisomeric forms of 1,3,7,9-tetraphospha-cyclodeca-1,2,7,8tetraene have been studied by theoretical methods.…”

Cover Picture: Catalytic Molecular Logic Devices by DNAzyme Displacement (ChemBioChem 7/2014)

“…Heterocyclic carbene chemistry has been reviewed,86 as have phosphorus Diels–Alder reactions 87. Cycloaddition reactions occurred with the reactive phosphine 111 (Scheme ), obtained by photolysis of 110 .…”