Premium
Isolation of a Cyclopentasilane from Magnesium Reduction of a Linear Hexasilane
Author(s) -
BallesteroMartínez Ernesto,
Ferguson John T.,
Siegler Maxime A.,
Klausen Rebekka S.
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100768
Subject(s) - chemistry , organosilicon , substituent , silylene , magnesium , stereochemistry , nuclear magnetic resonance spectroscopy , medicinal chemistry , organic chemistry , silicon
The reductive cyclization of two linear hexasilanes is contrasted, where a methylated precursor yielded a cyclohexasilane while the tert ‐butyl‐functionalized analog unexpectedly yielded a cyclopentasilane. A comprehensive analysis using X‐ray diffraction, IR, HR, HRMS, and multinuclear ( 1 H, 13 C and 29 Si) 1D and 2D NMR spectroscopy identified the 1,2‐dihydrodisilane t BuPhHSi‐SiHPh t Bu as an additional product, which was interpreted as supportive of a mechanism involving silylene elimination. The results of this study may prove informative about substituent effects in the practice of complex organosilicon molecular synthesis.