SiP-heterocycles derived from a bulky phosphanylsilylene.

Chem Commun (Camb)

College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, China.

Published: August 2023

AI Article Synopsis

  • The compound Bis(1-adamantyl)phosphanylsilylene (1) was heated with various alkynes under microwave conditions, leading to the creation of SiP-heterocycles (3a-d) that exhibit fluorescence and unique isomerization properties from silirene intermediates.
  • Additionally, reacting compound 1 with AdC≡P produced a heavy form of cyclopentadiene (4), a process that involves breaking a rarely seen Si(II)-P bond in silylene chemistry.
  • This study highlights new chemical transformations and properties associated with silylene derivatives, advancing the understanding of their reactivity and applications.

Article Abstract

Bis(1-adamantyl)phosphanylsilylene 1 was reacted with ArCCR (Ar = Ph, 4-iPr-CH, 3-F-CH; R = H, Ph) at 80 °C under microwave irradiation to afford fluorescence-active SiP-heterocycles 3a-d, which may undergo unique isomerizations starting from silirene intermediates. Moreover, the treatment of 1 with AdCP furnished a heavy congener of cyclopentadiene (4), whose formation involves cleavage of the Si(II)-P bond that is rarely observed in silylene chemistry.

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http://dx.doi.org/10.1039/d3cc02512hDOI Listing

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SiP-heterocycles derived from a bulky phosphanylsilylene.

Chem Commun (Camb)

August 2023

College of Material, Chemistry and Chemical Engineering, Key Laboratory of Organosilicon Chemistry and Material Technology, Ministry of Education, Hangzhou Normal University, Hangzhou, 311121, China.

Article Synopsis
  • The compound Bis(1-adamantyl)phosphanylsilylene (1) was heated with various alkynes under microwave conditions, leading to the creation of SiP-heterocycles (3a-d) that exhibit fluorescence and unique isomerization properties from silirene intermediates.
  • Additionally, reacting compound 1 with AdC≡P produced a heavy form of cyclopentadiene (4), a process that involves breaking a rarely seen Si(II)-P bond in silylene chemistry.
  • This study highlights new chemical transformations and properties associated with silylene derivatives, advancing the understanding of their reactivity and applications.
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