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• W2053666961 abstract "Primary and secondary α-chlorophosphines 2a−g are prepared in ca. 70% yield by chemoselective reduction of the corresponding phosphonic and phosphinic esters with AlHCl2 and are characterized by 31P, 13C, and 1H NMR and by HMRS. They can be kept several weeks in the refrigerator after purification. They lead then to the corresponding phosphaalkenes 3a−g by HCl elimination. For the volatile α-chlorophosphines 2a−e HCl elimination occurs in the gas phase on solid potassium carbonate under VGSR conditions (vacuum gas−solid reactions); the corresponding phosphaalkenes 3a−e are characterized by real time HRMS analysis of the gaseous flow (VGSR/HRMS coupling) and by solid-phase IR spectroscopy after condensation of the gaseous flow on a KBr window cooled to 77 K. The decomposition of phosphaalkenes at this temperature is monitored by IR spectroscopy. The α-chlorophosphines 2a−g undergo a HCl elimination in the liquid phase in the presence of a Lewis base; the formation of the transient phosphaalkenes is monitored by 31P FT-NMR. The temperature of HCl elimination is dependent both upon the P−H acidity of the phosphine precursors and the nature of the base. The 31P NMR data of the simple phosphaalkenes 3a−g are for the first time reported. They are consistent with the proposed structure. The stereochemistry of the (Z)- and (E)-isomers is established according to the “cis-rule”. Phosphaalkenes 3a−g are also characterized by chemical trapping in solution with various dienes, dipoles, or thiols. All of these experiments confirm the transient character of these species. The synthetic potential of this route is evaluated." @default.
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• W2053666961 date "1996-01-01" @default.
• W2053666961 modified "2023-10-16" @default.
• W2053666961 title "Dehydrochlorination of α-Chlorophosphines, a Simple and General Route to Phosphaalkenes" @default.
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• W2053666961 doi "https://doi.org/10.1021/ic960417z" @default.
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