The Addition of Nitrosyl Halides to Olefins. Dependence of Steric Course on Olefin Structure

Meinwald, Jerrold; Meinwald, Yvonne C.; Baker, T. N.

doi:10.1021/ja01073a033

Cited by 69 publications

(13 citation statements)

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“…The physicochemical characteristics of these compounds are consistent with those reported earlier. 1,[11][12][13] Reaction of norbornene 3 with the SOCl 2 -AgNO 3 system in acetonitrile. A solution of norbornene (0.19 g, 2 mmol) was added with vigorous stirring to a solution of AgNO 3 (0.34 g, 2 mmol) and SOCl 2 (0.24 g, 2 mmol) in acetonitrile (10 mL) at -40 °C.…”

Section: Methodsmentioning

confidence: 99%

“…The mother liquor was concentrated and the residue was chromatographed on a silica gel column (ethyl acetate-petroleum ether, 1 : 1). A mixture of N (syn 7 chloro exo bicyclo[2.2.1]hept 2 yl)acet amide (11) and N (anti 7 chloro exo bicyclo[2.2.1]hept 2 yl)acetamide (12) (R f 0.12) was obtained in a ratio of 5 : 1 in a yield of 0.115 g (30%). 1 ).…”

Section: Methodsmentioning

confidence: 99%

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New systems for classical nitrosohalogenation of alkenes 2. Generation of nitrosyl chloride in AgNO2-SOCl2 and AgNO3-SOCl2 systems

et al. 2005

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Study of the reactions of compounds of the norbornene series demonstrated that the AgNO 2 -SOCl 2 and AgNO 3 -SOCl 2 systems serve as nitrosochlorinating agents under the conditions of electrophilic addition. X ray diffraction study showed that dimerization of cis exo 2 chloro 3 nitrosobicyclo[2.2.1]heptane occurs heterostereospecifically. The origin of the active principle of the reagents is discussed.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

New systems for classical nitrosohalogenation of alkenes 2. Generation of nitrosyl chloride in AgNO2-SOCl2 and AgNO3-SOCl2 systems

et al. 2005

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“…A method for the isomerization of trans dimeric compounds to eis dimeric isomers is indicated in Section 5, Miscellaneous Preparation 11 [71].…”

Section: Free Radical Nitrosationmentioning

confidence: 99%

C-Nitroso Compounds

1971

Organic Chemistry: A Series of Monographs

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“…Under the present reaction conditions, exclusive formation of acetophenone oxime derivatives indeed rules out the possibility of the involvement of NO + in the initial stage of the reaction, which would otherwise lead to the formation of 2-phenylacetaldehyde oxime and its derivatives on addition to substituted ethylenes. 13 Hydrogen evolution has also been observed in the initial stage of the reaction on addition of NaBH 4 in the presence of MeOH-H 2 O (5 : 1). The determining step in the mechanism is the addition of olefin to the metal centre of the iron-dipic complex (A) that leads to the formation of σ-alkyliron(III) complex (B).…”

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confidence: 94%

“…7d Other hydrogenation side-products, resulting from the reduction Scheme 1 An outline for the catalytic transformation of 1 to 2. † Electronic supplementary information (ESI) available: General procedure, characterization data and 1 H and 13 C-NMR spectra of 2a-2u. See DOI: 10.1039/ c3dt51764k…”

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confidence: 99%