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Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes

Journal Article


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Abstract


  • The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl P-electrophiles are tolerated in reasonable to excellent yields.

Authors


Publication Date


  • 2015

Citation


  • Gregson, A. M., Wales, S. M., Bailey, S. J., Willis, A. C. & Keller, P. A. (2015). Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes. Journal of Organic Chemistry, 80 (19), 9774-9780.

Scopus Eid


  • 2-s2.0-84942869869

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4322&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3299

Number Of Pages


  • 6

Start Page


  • 9774

End Page


  • 9780

Volume


  • 80

Issue


  • 19

Abstract


  • The reaction between 1,4-di-Grignard reagents and phosphonous(III) dichlorides is a classical method for the direct synthesis of phospholanes. Reported here is an extension of this approach to the preparation of value-added, annulated phospholane oxides, achieved through the combination of carbocyclic-fused di-Grignard reagents and readily available phosphonic(V) dichlorides. The procedure is amenable to (benz)annulation at both the 2,3- and 3,4-positions of the phospholane ring, and a variety of aliphatic, cyclic and aryl P-electrophiles are tolerated in reasonable to excellent yields.

Authors


Publication Date


  • 2015

Citation


  • Gregson, A. M., Wales, S. M., Bailey, S. J., Willis, A. C. & Keller, P. A. (2015). Cyclic phosphine oxides and phosphinamides from di-grignard reagents and phosphonic dichlorides: modular access to annulated phospholanes. Journal of Organic Chemistry, 80 (19), 9774-9780.

Scopus Eid


  • 2-s2.0-84942869869

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4322&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3299

Number Of Pages


  • 6

Start Page


  • 9774

End Page


  • 9780

Volume


  • 80

Issue


  • 19