Oxidative addition reactions of cyclic chlorophosphites and arsenites with diols and 1,2-quinones: X-ray structure of the phosphocin (ClCH2CMe2CH2O)P(O) {(O-2,4-(t-bu)2C6H2)2CH2}

Said, Musa A. ; Kumara Swamy, K. C. ; Chandra Mohan, K. ; Venkata Lakshmi, N. (1994) Oxidative addition reactions of cyclic chlorophosphites and arsenites with diols and 1,2-quinones: X-ray structure of the phosphocin (ClCH2CMe2CH2O)P(O) {(O-2,4-(t-bu)2C6H2)2CH2} Tetrahedron, 50 (23). pp. 6989-6998. ISSN 0040-4020

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Official URL: http://linkinghub.elsevier.com/retrieve/pii/S00404...

Related URL: http://dx.doi.org/10.1016/S0040-4020(01)81351-X

Abstract

The phosphorinane ring opens when CIP(OCH2CMe2CH2O) (1) is treated with diols and N-chlorodiisopropylamine (NCDA) or with quinones. X-ray structure of one such product, the phosphocin oxide, (ClCH2CMe2CH2O) P(O) {(O-(2,4-(? -bu)2C6H2)2CH2} (3) reveals a 'symmetrical anti' (chair) conformation of the eight membered ring. The phenylene phosphorochloridite CIP(O2C6H4) by contrast gives pentacoordinated phosphoranes in similar reactions. The arsorinane ClAs(OCH2CMe2CH2O) (9) on treatment with 2,2-dimethyl-1,3-propanediol-NCDA affords an arsorane formulated as ClAs(OCH2CMe2CH2O)2; no reaction was apparent when 9 was treated with quinones.

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