Abstract
With the aim of synthesizing novel functionalized derivatives of phosphinine (phosphabenzene), we investigated Diels-Alder approaches to 2-halophosphinines. The reaction of dienes such as 1-isopropenyl-1-cyclohexene and 1-vinylnaphthalene with Cl2P-CHCl2 and triethylamine gave 2-chlorophosphinines, but their substitution pattern was unsuitable for the synthesis of bidentate phosphinine ligands. However, the precursor Cl2P-CHl2 reacted with triethylamine in the presence of 1,3-butadiene or its 2,3-dimethyl derivative to furnish 2-iodophosphinines 5 which, directly or after formation of their pentacarbonyltungsten complexes, underwent a number of interesting functionalization reactions. Useful for reaction with a number of electrophiles were the organozinc reagent 4,5-dimethyl-2-iodozincophosphinine (26) which could be obtained directly from the corresponding 2-iodophosphinine 5b and zinc either in DMF or in THF/TMEDA, and the pentacarbonyltungsten coordinated 2-lithio derivative 36.
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
