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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 190, 2015 - Issue 5-6: 20th International Conference on Phosphorus Chemistry (ICPC-2014)
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Original Articles

The 3JCCNP Coupling Constants of Pentacoordinate Spirophosphorane Derivatives: As a Method to Assign Relative Configuration

Shuxia CaoCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. ChinaCorrespondence[email protected]
,
Zhongfei ZhouCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. China
,
Wang DaiCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. China
,
Pei ZhaoCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. China
,
Yanchun GuoCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. China
&
Yufen ZhaoCollege of Chemistry and Molecular Engineering, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan Province, P. R. China;Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, P. R. China
Pages 925-931 | Received 22 Aug 2014, Accepted 20 Nov 2014, Published online: 01 Jul 2015
 
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GRAPHICAL ABSTRACT

Abstract

The phosphorus-carbon coupling constant 3JCCNP was found to be sensitive to the relative configuration of pentacoordinate spirophosphorane diastereoisomers, while the 2JCNP value remained almost unchanged. The 3JCCNP value of the spirophosphorane with ΛP configuration at phosphorus was obviously larger than that with ΔP configuration. The rule, 3JCCNP (ΛP) > 3JCCNP (ΔP), for pentacoordinate spirophosphorane diastereoisomers was used to assign the configurations of new alkoxy spirophosphorane derivatives, and satisfactory results were achieved. The results showed that the coupling constant 3JCCNP might be used as a reliable probe for the configuration of pentacoordinate spirophosphorane derivatives.

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