Anodic oxidation of aryl propargyl and aryl allyl ethers at a platinum electrode
TL;DR: In this article, the oxidation reactions of aromatic 3,3-sigmatropic systems have been investigated under different conditions viz, (a) anodic oxidation in amphipr
About: This article is published in Tetrahedron.The article was published on 1994-01-01. It has received 5 citations till now. The article focuses on the topics: Propargyl & Aryl.
Citations
More filters
392 citations
TL;DR: In this paper, the successful mononitration of a variety of electron-rich aromatic substrates was reported, employing either nitronium tetrafluoroborate or "claycop" as the nitrating agent.
30 citations
TL;DR: In this article, the nitration of N,N−dialkylanilines with NaNO2 using water as the solvent has been achieved in good to excellent yields at ambient temperature.
6 citations
TL;DR: The enol-lactone dimer as discussed by the authors was derived from carbonylative coupling of two molecules of norbornene, which has not been recorded before under these conditions appears likely to be an overlooked by-product of many Pauson-Khand reactions.
5 citations
TL;DR: In this paper, the oxidation reactions of aromatic 3,3-sigmatropic systems have been investigated under different conditions viz., (a) anodic oxidation in amphipr
Abstract: The oxidation reactions of aromatic 3,3-sigmatropic systems have been investigated under different conditions viz. , (a) anodic oxidation in amphipr
References
More filters
TL;DR: The vinyl proton of the E isomers 5 were consistently shifted downfield -1 .O ppm from the corresponding Z isomers 6: G. Buchi and H. Wuest, Helv.
Abstract: (1) Part 3 of a series on pheromone synthesis. For part 2 see P. J. Kocienski and G. J. Cernigliaro, J. Org. Cbem., 41, 2927 (1976). (2) H. M. Fales, M. S. Blum, R. M. Crewe, and J. M. Brand, J. lflsect Pbysiol., 18, 1077 (1972). (3) J. A. Katzeneilenbogen and T. Utawanit, J. Am. Cbem. Soc., 96, 6153 (1974). (4) L. A. Carpino, J. Am. Cbem. SOC., 80,601 (1958); L. A. Carpino, P. H. Terry, and S. D. Thette, J. Org. Cbem., 31, 2867 (1966). (5) L. A. Carpino and E. G. S. Rundberg, J. Org. Cbem., 34, 1717 (1969), investigated some bicyclic halopyrazolinones in which R, and R2 were alkyl groups which formed part of a ring. in these cases, the €isomer was the exclusive product. (6) For a review see D. J. Cram, \"Fundamentals of Carbanion Chemistry\", Academic Press, New York, N.Y., 1965, pp 130-135. (7) The procedure used for the preparation of 7 was derived from A. P. Krapcho, J. Diamanti, C;. Cayen, and R. Bingham, \"Organic Syntheses\", Collect. Vol. V, Wiley. New York. N.Y., 1973, p 198: bp 102-105 OC (20 mm); ir(CC14) 1750, 1720 cm-'; NMR (CCI4) 6 3.7 (s, 3 H), 3.7 (q, 1 H), 2.7 (quintet, 1 H), 1.6(m,2H),1.3(d,3H),1.1(d,3H),O.9(t,3H). (8) The vinyl proton of the E isomers 5 were consistently shifted downfield -1 .O ppm from the corresponding Z isomers 6: G. Buchi and H. Wuest, Helv. Cbim. Acta, 50, 2440 (1967). (91 An alternative to the Scheme I mechanism entails hydrolytic cleavage of 2 to the vinyl diimide i which may then undergo radical decomposition to the observed products. ESR studies have shown that vinyl radicals invert
263 citations
258 citations
185 citations
TL;DR: In this article, the reagent in methanol with monohydric phenols directly yields p -quinone ketals, also in good yields, and 4-alkyl-4-methoxycycloxycyclohexadienones.
140 citations
TL;DR: In this article, two mechanisms are proposed for the dimerization of cation radicals of anisoles and related compounds, termed as radical-substrate coupling (RSC) and radical-surface coupling (RRD).
Abstract: Publisher Summary The dimerization of cation radicals of simple benzene derivatives is usually accompanied by the formation of the corresponding biphenyl derivative. This, by virtue of the extended conjugation is more easily oxidized, and frequently only intractable tars are found as final products. If the reaction medium is carefully selected, so that the biphenyl cation radicals are stable, useful synthetic procedures can be developed. Two mechanisms are probable for the dimerization of cation radicals of anisoles and related compounds. They are termed “radical–radical dimerization” (RRD) and “radical–substrate coupling” (RSC). The oxidation of aromatic hydrocarbons and alkylaromatic compounds in media of low nucleophilicity results in the formation of dimers. The cation radicals of triphenylamines form dimers in high yield when generated in acetonitrile. The products are tetraphenylbenzidines.
137 citations