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Studies on the preparations of organophosphorus compounds from triphenylphosphine oxide

Jian-Qiu Zhang 筑波大学 DOI:10.15068/0002002121

2021.12.02

概要

Organophosphine oxides are a class of pentavalent phosphorus compounds with the formula R3P(O) possessing one P=O bond and three P-R bonds wherein R is generally alkyl or aryl group, featuring tetrahedral structure with phosphorus atom at the center (Scheme 1.1).1 Calculation and experimental studies have indicated that the P=O bond can be described as one highly polarized σ-bond plus strong back-bond of the oxygen π orbitals, and thus a highly ionic dative R3P+‒O¯ is better than the traditional double bond to depict phosphine oxides.1 Generally, there are three kinds of phosphine oxides (primary, secondary and tertiary phosphine oxides) shown in Scheme 1.1, among which tertiary phosphine oxides are the most studied and applied because of their strong chemical stability and diversity, whereas the primary and secondary phosphine oxides are usually used as starting materials for the preparation of other organophosphorus compounds.

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[9] The slightly lower yield of TPO prepared by one-pot was attributed to side reactions of Ph2P(O)H and MesCOCl generating Ph2PCl. See: Zhang, J.-Q., Yang, S., Han, L.-B. Tetrahedron Lett. 2020, 61,151556.

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[11] In industrial applications, the most significant acylphosphine oxide photoinitiators are diphenyl(2,4,6- trimethylbenzoyl)phosphine oxide (TPO), ethyl(2,4,6-trimethylbenzoyl) phenylphosphinate (TPO-L) and phenylbis(2,4,6-trimethylbenzoyl)phosphine oxide (BAPO). See: Introduction of acylphosphine oxide photoinitiator. http://www.sellchems.com/acylphosphine-oxide-photoinitiator/

[12] Ph2P-O-SiMe3 was isolated in pure form, see SI. (a) Thottathil, J. K., Przybyla, C. A., Moniot, J. L. Tetrahedron Lett. 1984, 25, 4737–4740. (b) Issleib, K., Walther, B. J. Organomet. Chem. 1970, 22, 375–386.

[13] Musina, E. I., Shamsieva, A.V., Balueva, A. S., Karasik, A. A. Tertiary Phosphines: Preparation and Reactivity. Organophosphorus Chem. 2020, 49, 1–63.

[14] Montgomery, R. E., Quin, L. D. J. Org. Chem., 1965, 30, 2393–2395.

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