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Original Articles

Synthesis of phosphorus- and sulfur-stabilized carbone (Me)Ph2P→C←SPh2(= NMe)

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Pages 159-162 | Received 31 Aug 2015, Accepted 01 Oct 2015, Published online: 06 Feb 2016
 

GRAPHICAL ABSTRACT

Abstract

Iminosulfane(phosphane)carbon(0) (iSPC) [(Me)Ph2P→C←SPh2(= NMe): 1] is generated by the deprotonation of corresponding cationic salt 1·H, which is obtained from the reaction of iminosulfonium methylide with Ph2PCl and subsequent P-methylation. Density functional theory calculations reveal that the electronic structure of 1 has two lone pairs of electrons at the carbon center. First and second proton affinity values are theoretically calculated to be 287.2 and 187.0 kcal mol−1, respectively. The highest occupied molecular orbital (HOMO) energy level of 1 is higher energy than that of bis(iminosulfane)carbon(0) (BiSC: [(MeN =)Ph2S→C←SPh2(= NMe)]). The reactivities of these lone pairs of electrons are demonstrated by the C-diaurated complex.

ACKNOWLEDGEMENTS

This work was partially supported by Grants-in-AID for Scientific Research(c) (NO.15K05438) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and research fellow of the Japan Society for the Promotion of Science for Young Scientists (NO.15J05047).

Funding

This work was partially supported by Grants-in-AID for Scientific Research(c) (No.15K05438) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and research fellow of the Japan Society for the Promotion of Science for Young Scientists (No.15J05047).

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