Six-membered cyclic phosphate-phosphonates: Synthesis and stereochemistry of cis/trans-2-phosphorylbenzyloxy-4-aryl-5,5-dimethyl-1,3,2λ 5-dioxaphosphorinane-2-thiones (selones)

Jia Zhou, Ruyu Chen

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A study on the synthesis and stereochemistry of the novel six-membered cyclic phosphate-phosphonates, cis/trans-2-phosphorylbenzyloxy-4-aryl-5,5-dimethyl-1,3,2λ 5-dioxaphosphorinane-2-thiones (selones) 7a-f has been carried out. The title compounds were obtained in good overall yields by a one-pot procedure using tris(diethylamino)phosphine activated by iodine as the phosphorylating and ring-closing reagent. Their geometric stereoisomers were isolated and characterized. A cis-configuration and a preferred chair conformation of one isomer of 7b have been established by X-ray diffraction analysis. This study also gives a good explanation for the correlation between the configurational assignments and the chemical shifts of C4-H and 31P, which shows some difference from previously reported results.

Original languageEnglish (US)
Pages (from-to)2917-2921
Number of pages5
JournalJournal of the Chemical Society - Perkin Transactions 1
Issue number17
StatePublished - Sep 7 1998
Externally publishedYes

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Thiones
Organophosphonates
Stereochemistry
Stereoisomerism
Chemical shift
Iodine
Isomers
X ray diffraction analysis
Conformations
Phosphates
tris(diethylamino)phosphine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Six-membered cyclic phosphate-phosphonates: Synthesis and stereochemistry of cis/trans-2-phosphorylbenzyloxy-4-aryl-5,5-dimethyl-1,3,2λ 5-dioxaphosphorinane-2-thiones (selones)",
abstract = "A study on the synthesis and stereochemistry of the novel six-membered cyclic phosphate-phosphonates, cis/trans-2-phosphorylbenzyloxy-4-aryl-5,5-dimethyl-1,3,2λ 5-dioxaphosphorinane-2-thiones (selones) 7a-f has been carried out. The title compounds were obtained in good overall yields by a one-pot procedure using tris(diethylamino)phosphine activated by iodine as the phosphorylating and ring-closing reagent. Their geometric stereoisomers were isolated and characterized. A cis-configuration and a preferred chair conformation of one isomer of 7b have been established by X-ray diffraction analysis. This study also gives a good explanation for the correlation between the configurational assignments and the chemical shifts of C4-H and 31P, which shows some difference from previously reported results.",
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AU - Chen, Ruyu

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