Bisphosphine monoxides (BPMOs) are hemi-labile ligands possessing both hard and soft donor sites. A number of BPMOs have also proven useful in synthesis, analytical chemistry, materials chemistry, and in cancer and AIDS research. Synthetic routes are limited since pathways utilizing normal oxidizers (e.g., hydrogen peroxide) are plagued by mixtures of monoxide and dioxide products in addition to remaining bisphosphine precursor. Many of these routes are expensive and included difficult or sensitive isolation protocols. A simple, open-air approach has been developed that does not require a metal catalyst or air-/moisture-sensitive precursors to produce BPMOs in high purity. The two-step process begins by first preparing a monophosphonium salt from an α-bromoester. Following isolation, the monophosphonium salt was utilized in an aqueous Wittig reaction with benzaldehyde to selectively oxidize one phosphorus center. Monoxides of the commonly utilized alkane-linked bisphosphines, Ph2P(CH2)nPPh2 (n = 1-4, 6) and bis(diphenylphosphino)benzene have been isolated in good to excellent yields. 31P{1H} NMR has been used as the primary means to characterize products and identify distributions of unoxidized and dioxide impurities.

Monophosphonium salts of bisphosphines as facile precursors to bisphosphine monoxides

Macromolecular Chemistry: The Second Century

[Author Benefits](https://scimeetings.acs.org/?utm_source=pubs_content_marketing&utm_medium=website&utm_campaign=0320_MCF_NPI_Launch_Spring_Homepage&ref=pubs_content_marketing)

[How to use SciMeetings](https://storage.googleapis.com/dl.morressier.com/acs/SciMeetings-ACSSpring2020-HowToGuide_M3020-Final.pdf)

[Frequently Asked Questions](https://storage.googleapis.com/dl.morressier.com/acs/SciMtng_ACSNMSp2020_FAQ_M3120_Final.pdf)

ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.