Open AccessSqualene interactions with some hydrosilanes and hydrogermans
Author(s) -
D. A. Efimenko,
Ssc Rf Jsc,
I. B. Sokol’skaya,
Mihail M. Sibircev,
Valentin G. Lahtin,
П. А. Стороженко,
Evgeny N. Oficerov,
Antonida V. Kalistratova,
Vladislav Y. Kolesnikov,
GNIIChTEOS,
Ssc Rf Jsc GNIIChTEOS
Publication year - 2020
Publication title -
butlerovskie soobŝeniâ
Language(s) - English
Resource type - Journals
ISSN - 2074-0212
DOI - 10.37952/roi-jbc-01/20-64-11-42
Subject(s) - markovnikov's rule , chemistry , squalene , hydrosilylation , reactivity (psychology) , electrophile , regioselectivity , electronegativity , adduct , medicinal chemistry , alkoxy group , alkyl , silicon , stereochemistry , photochemistry , catalysis , organic chemistry , medicine , alternative medicine , pathology
Squalene hydrosilylation by a number of organohydrosilanes R3SiH and Me3GeH, including a mixture of α- and β-isomers of adducts of vinyltrimethylsilane addition to tetramethyldisiloxane: HSi(Me2)O(Me2)Si-C(Me)-SiMe3 and HSi(Me2)O(Me2)Si-(CH2)2-SiMe3, formed both according to Markovnikov's rule and against it, is discussed. We pay attention to the mismatch of values between the electronegativities of carbon, silicon, germanium and hydrogen atoms and the reactivity of C-H, Si-H, and Ge-H bonds. A spectral study of a mixture of α- and β-isomers was carried out. The effect of substituents at elements on its reactivity is discussed: hydrosilanes with chlorine atoms, alkyl and alkoxy groups on silicon are not active in the squalene hydrosilylation. In contrast to them, the α- and β-adducts and their mixture add well to squalene with an unambiguously unknown regioselectivity. The results obtained indicate the special behavior of squalene in electrophilic addition reactions catalyzed by metal complexes, in contrast to substituted ethylenes.