Reaction of silylallenes with triplet molecular oxygen

A facile formal ene reaction of trisubstituted silylallenes with triplet molecular oxygen involving the cleavage of a H-C(sp(2)) bond has been described. For this formal ene reaction, the silyl substituent was found to be critical to induce peroxide formation. DFT calculations clearly show the drama...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 5; no. 17; pp. 2542 - 2546
Main Authors Xia, Yuanzhi, Lee, Nam-Kyu, Sabbasani, Venkata R., Gupta, Saswata, Lee, Daesung
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 07.09.2018
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Hydrogen bonds
Organic chemistry
Oxygen
Peroxide
Physical Sciences
Science & Technology
AMARYLLIDACEAE ALKALOIDS
ALLENYLSILANES
ALLENIC C(SP)-H BOND
LEWIS-ACID
PHOTOSENSITIZED OXYGENATION
IMINO ENE REACTION
SINGLET OXYGEN
CAROTENOIDS
C-H AMINATION
VINYL HYDROGEN
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Summary:A facile formal ene reaction of trisubstituted silylallenes with triplet molecular oxygen involving the cleavage of a H-C(sp(2)) bond has been described. For this formal ene reaction, the silyl substituent was found to be critical to induce peroxide formation. DFT calculations clearly show the dramatic weakening of the allenic C(sp(2))-H bond by the -silyl group.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/c8qo00390d