Novel Ylidic Phosphoryl compounds from Halogenated Furan-2,5-Diones with Trivalent Phosphorus Esters: Application of this approach to new Trisphosphonates containing a Geminal Bisphosphonate Unit

Vaughan Griffiths, D.; Benoit, David M.; Cheong, Yuen Ki; Duncanson, Philip; Han, Xiao

Abstract

The reactions of trivalent phosphorus esters, including trialkyl phosphites, dialkyl phosphonites, and alkyl phosphinites, with 3-halo- and 3,4-dihalo-furan-2,5-diones has been shown to lead to the formation of novel phosphorus ylides possessing additional phosphoryl-containing groups. For the reaction of 3,4-dihalo-furan-2,5-diones with trialkyl phosphites, the products are trialkoxyphosphonium ylides containing an adjacent geminal bisphosphonate unit. These can be used to provide a convenient route to novel 2,3,3-tris(dialkoxyphosphoryl)-substituted propionate esters which can be hydrolyzed to give the corresponding novel trisphosphonic monocarboxylic acid.

Citation

Vaughan Griffiths, D., Benoit, D. M., Cheong, Y. K., Duncanson, P., & Han, X. (2014). Novel Ylidic Phosphoryl compounds from Halogenated Furan-2,5-Diones with Trivalent Phosphorus Esters: Application of this approach to new Trisphosphonates containing a Geminal Bisphosphonate Unit. Phosphorus, sulfur, and silicon and the related elements, 189(7-8), 1013-1027. https://doi.org/10.1080/10426507.2014.905570

• Acceptance Date: Feb 25, 2014
• Online Publication Date: Aug 4, 2014
• Publication Date: Aug 3, 2014
• Deposit Date: Dec 13, 2017
• Publicly Available Date: Dec 15, 2017
• Journal: Phosphorus, Sulfur, and Silicon and the Related Elements
• Print ISSN: 1042-6507
• Electronic ISSN: 1563-5325
• Publisher: Taylor and Francis
• Peer Reviewed: Peer Reviewed
• Volume: 189
• Issue: 7-8
• Pages: 1013-1027
• DOI: https://doi.org/10.1080/10426507.2014.905570
• Keywords: Halogenated furan-2,5-diones; Trivalent phosphorus esters; Ylides; Geminal bisphosphonates; Trisphosphonates
• Public URL: https://hull-repository.worktribe.com/output/502515
• Publisher URL: http://www.tandfonline.com/doi/abs/10.1080/10426507.2014.905570
• Additional Information: Peer Review Statement: The publishing and review policy for this title is described in its Aims & Scope.; Aim & Scope: http://www.tandfonline.com/action/journalInformation?show=aimsScope&journalCode=gpss20