2000
DOI: 10.1016/s0040-4020(00)00008-9
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Factors in Molecular Structure to Activate Nitro Compounds for Organic Transformations

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Cited by 6 publications
(3 citation statements)
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“…This behaviour exerted by silicon has been shown to be of general utilisation in the chemistry of nitro compounds as demonstrated for the conversion of 79 into cyclohexanone 80. 49 It has recently been observed, however, that the 7-diaryl-5-nitronorbornene exo-81 actually does give as the main product the ketone exo-82 arising from a Nef reaction, along with the lactone exo-83 and some unreacted nitro derivative (13%) (Scheme 24). 50 Interestingly, the reaction of endo-81 under the same conditions affords exclusively endo-83 in 87% yield (Scheme 25).…”
Section: Other Methodsmentioning
confidence: 99%
“…This behaviour exerted by silicon has been shown to be of general utilisation in the chemistry of nitro compounds as demonstrated for the conversion of 79 into cyclohexanone 80. 49 It has recently been observed, however, that the 7-diaryl-5-nitronorbornene exo-81 actually does give as the main product the ketone exo-82 arising from a Nef reaction, along with the lactone exo-83 and some unreacted nitro derivative (13%) (Scheme 24). 50 Interestingly, the reaction of endo-81 under the same conditions affords exclusively endo-83 in 87% yield (Scheme 25).…”
Section: Other Methodsmentioning
confidence: 99%
“…6 In certain transformations, a γ-silyl group is eliminated from the substrate. 7 Examples include 1,4elimination of γ-silyl alcohols by use of ceric ammonium nitrate 8 as well as ring opening of γ-silyl cyclopropyl 9 and cyclobutyl 10 ketones by Lewis acids. Herein, we report our new findings on the Lewis acid-catalyzed transformations of various γ-silyl nitro compounds 11 to benzofuran oximes, to benzo[b]thiophene oximes, and to multisubstituted dihydrofurans.…”
mentioning
confidence: 99%
“…Reactions involving the γ-effect of silicon are limited, such as in the Nef reaction, TiCl 4 -catalyzed arylation of 1,4-benzoquinones, and norbornyl solvolyses . In certain transformations, a γ-silyl group is eliminated from the substrate . Examples include 1,4-elimination of γ-silyl alcohols by use of ceric ammonium nitrate as well as ring opening of γ-silyl cyclopropyl and cyclobutyl ketones by Lewis acids.…”
mentioning
confidence: 99%