Formation of silicon centered spirocyclic compounds: reaction of N-heterocyclic stable silylene with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine.

Content Provider	Semantic Scholar
Author	Azhakar, Ramachandran Sarish, Sankaranarayana Pillai Tavčar, Gašper Roesky, Herbert W. Hey, Jakob Stalke, Dietmar Koley, Debasis
Copyright Year	2011
Abstract	Three silicon centered spirocyclic compounds 1-3, possessing silicon fused six- and five-membered rings have been prepared by the reaction of NHSi (L) [L = CH{(C=CH(2))(CMe)(2,6-iPr(2)C(6)H(3)N)(2)}Si] with benzoylpyridine, diisopropyl azodicarboxylate, and 1,2-diphenylhydrazine, respectively, in a 1:1 ratio. The three spirocyclic compounds (1- 3) were obtained by three different pathways. The reaction of L with benzoylpyridine leads to the activation of the pyridine ring, and dearomatization occurred. Treatment of diisopropyl azodicarboxylate with L favors a [1 + 4]- rather than a [1 + 2]-cycloaddition product, and the azo compound was converted to hydrazone derivative. Finally the reaction of 1,2-diphenylhydrazine and L results in the elimination of hydrogen by activating one of the C-H bonds present in the phenyl ring. All three complexes 1- 3 were characterized by single crystal X-ray structural analysis, NMR spectroscopy, EI-MS spectrometry, and elemental analysis. In addition the optimized structures of probable products and possible intermediates were investigated using density functional theory (DFT) calculations.
File Format	PDF HTM / HTML
DOI	10.1021/ic102566c
PubMed reference number	21391579
Journal	Medline
Volume Number	50
Issue Number	7
Alternate Webpage(s)	https://goedoc.uni-goettingen.de/bitstream/handle/1/9429/Formation%20of%20Silicon%20Centered%20Spirocyclic%20Compounds%20Reaction%20of.pdf?sequence=4
Alternate Webpage(s)	https://doi.org/10.1021/ic102566c
Journal	Inorganic chemistry
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article