1990
DOI: 10.1002/chin.199040108
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ChemInform Abstract: Reaction of Nitronium Tetrafluoroborate with 4‐Acyloxy‐2‐methyl‐1‐butenes.

Abstract: The reaction specified in the title affords separable mixtures of the fluoronitro derivatives (III) and the hydroxynitro derivatives (IV), which are formed via unstable 1,3‐dioxane derivatives, which can be detected by low‐temp.

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Cited by 3 publications
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“…Similar fluorinations using NO 2 BF 4 have also been reported with homoallylic esters 347 , giving the corresponding β-nitro fluorides 349 in moderate yield (three examples, 41–73%). As before, β-nitro alcohols were also formed as byproducts from competitive hydrolysis of the putative 1,3-dioxan-2-ylium ion intermediate 348 during the aqueous workup (Scheme ) …”
Section: Additions To Alkenes Alkynes and Allenesmentioning
confidence: 87%
“…Similar fluorinations using NO 2 BF 4 have also been reported with homoallylic esters 347 , giving the corresponding β-nitro fluorides 349 in moderate yield (three examples, 41–73%). As before, β-nitro alcohols were also formed as byproducts from competitive hydrolysis of the putative 1,3-dioxan-2-ylium ion intermediate 348 during the aqueous workup (Scheme ) …”
Section: Additions To Alkenes Alkynes and Allenesmentioning
confidence: 87%
“…Furthermore, reactions of allylic esters (134a ± d) 122 and homoallylic esters (134e ± g) 123 with nitronium tetrafluoroborates followed by hydrolysis have been reported; they gave mixtures of 2-fluoro nitro alkane (X = F) and b-nitro alcohol (X = OH) derivatives 135a ± g. In this case, the overall yield and composition of the products depend on the bulk of the acyl substituent R. The reaction presumably occurs via cyclic cationoid intermediates 136a ± g, which are split by fluoride or hydroxide ions to give the final products. The formation of these intermediates was detected using low-temperature NMR spectroscopy.…”
Section: And References Cited Therein)mentioning
confidence: 99%
“…The formation of these intermediates was detected using low-temperature NMR spectroscopy. 123 Compound Acetonitrile may serve as the nucleophile which completes the reaction of alkenes with NO 2 BF 4 . For example, low-temperature treatment of substituted styrenes with nitronium tetrafluoroborate in MeCN followed by decomposition with saturated aqueous NaHCO 3 afforded the corresponding nitro acetamides 137 obviously formed by the Ritter reaction.…”
Section: And References Cited Therein)mentioning
confidence: 99%
“…132 Treatment of unsaturated ketones 180 with nitronium tetrafluoroborate at 730 8C in a solution in SO 2 followed by treatment with water gives compounds 181 in low yields. 133 An original method has been proposed 134 . The reaction of ethyl 4-methylpent-2-enoate 183 with nitryl chloride or nitrosyl chloride yields nitrite 184, which is converted into compound 185 on refluxing with water, the overall yield of the latter being 34%.…”
Section: Synthesis Of Nitro Alcohols By Simultaneous Introduction Of ...mentioning
confidence: 99%