Reactions of an Isolable Dialkylsilylene with Aroyl Chlorides. A New Route to Aroylsilanes

Xu-Qiong Xiao; Xupeng Liu; Qiong Lu; Zhifang Li; Guoqiao Lai; Mitsuo Kira

doi:10.3390/molecules21101376

Reactions of an Isolable Dialkylsilylene with Aroyl Chlorides. A New Route to Aroylsilanes

Molecules. 2016 Oct 15;21(10):1376. doi: 10.3390/molecules21101376.

Authors

Xu-Qiong Xiao¹, Xupeng Liu², Qiong Lu³, Zhifang Li⁴, Guoqiao Lai⁵, Mitsuo Kira⁶

Affiliations

¹ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. xqxiao@hznu.edu.cn.
² Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. lxpyoujigui@163.com.
³ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. ahbzmclq@163.com.
⁴ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. zhifanglee@hznu.edu.cn.
⁵ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. gqlai@hznu.edu.cn.
⁶ Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China. mkira@m.tohoku.ac.jp.

Abstract

The reactions of isolable dialkylsilylene 1 with aromatic acyl chlorides afforded aroylsilanes 3a-3c exclusively. Aroylsilanes 3a-3c were characterized by ¹H-, ¹³C-, and ²⁹Si-NMR spectroscopy, high-resolution mass spectrometry (HRMS), and single-crystal molecular structure analysis. The reaction mechanisms are discussed in comparison with related reaction of 1 with chloroalkanes and chlorosilanes.

Keywords: X-ray analysis; acylsilane; dialkylsilylene; insertion; silyl ketone.

MeSH terms

Chlorides / chemistry*
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Organosilicon Compounds / chemistry*
Silanes / chemistry*

Substances

Chlorides
Organosilicon Compounds
Silanes