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Synthesis 1993; 1993(12): 1247-1252
DOI: 10.1055/s-1993-26036
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Organophosphorus Compounds; 72.1 The Tri-tert-butylcyclopropenyl Group as a Steric Protecting Function for 1-Phosphaallenes

Michael Hafner* , Thomas Wegemann, Manfred Regitz
  • *Fachbereich Chemie der Universität Kaiserslautern, Erwin-Schrödinger-Straße, D-67 663 Kaiserslautern, Germany
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Publication Date:
29 April 2002 (online)

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When the tri-tert-butylcyclopropenylphosphane 5 is allowed to react with ketenes 6, the cyclopropenyl(silyl)vinylphosphanes 7 are obtained. Subsequent acylation proceeds via silyl exchange to furnish the phosphanes 8 while methanolysis gives rise to the secondary phosphanes 9 by way of P/Si bond cleavage. Sodium hydroxide catalyzed elimination of hexamethyldisiloxane from 7 results in the formation of the 1-phosphaallenes 10. The P/C double bonds of the latter can be saturated by either 1,2-addition (→ 11, 12) or by oxidative addition (→ 13) followed by addition of water (→ 14). Complexation of 10 with the metal fragments W(CO)5 or Fe(CO)4 moieties yields the novel metal complexes 15 and 16.