ChemInform Abstract: REACTIVITY OF ORGANOTIN COMPOUNDS. XXII. REACTIONS OF ORGANOTIN COMPOUNDS WITH O‐NITROPHENYLSULFENYL CHLORIDE

Kashin, A. N.; Бумагин, Н. А.; Beletskaya, I. P.; Reutov, O. A.

doi:10.1002/chin.198114144

Cited by 8 publications

(21 citation statements)

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“…Alternatively, one can consider converting the enol ether to an electrophilic intermediate and trapping it with a nucleophile. Such a strategy was first reported in 1982, with the dimerization reaction of a stannyl enol ether promoted by PIDA (Scheme ) …”

Section: Enol Substratesmentioning

confidence: 99%

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Lauriers

Legault

2016

Asian J Org Chem

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This reviewisd edicated to Prof. Jean Lessard on the occasion of his 80th birthday Asian Abstract: In numerous iodine(III)-mediated methodologies that involve ketone compounds, the enol tautomer is expected to be the reactive species. In this context,t he exploration of enol and ynol surrogates as substrates is of great interest. Activated p-systems have been shown to exhibit interesting and highly exploitable behavior towardh ypervalent iodine reagents. This has led to the development of nu-merousu seful oxidativet ransformations. Enamines, enamides, enol derivatives, haloalkenes, and haloalkynes are all enol or ynol surrogates that are reactivet owards the most populari odanes and iodonium salts. This Focus Review will describep ast and on-going research involving these substrates to gain insighti nto the similarities and disparities observed in their reactivity profiles.The ORCID identification number(s) for the author(s) of this articlecan be found under http://dx.Scheme4.Proposed mechanism to explain 2 H-arizine formation and acetoxylation.Scheme5.Synthesis of 2-trifluoromethyloxazoles developed by Du, Zhao, and co-workers.Scheme6.Dichlorination of enaminesd evelopedbyZ hao, Du, and co-workers.Scheme7.Optimizedreductive conditionst oconvertthe dihaloimines to their corresponding enamines.

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Section: Enol Substratesmentioning

confidence: 99%

Enol and Ynol Surrogates: Promising Substrates for Hypervalent Iodine Chemistry

Lauriers

Legault

2016

Asian J Org Chem

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“…The N-nitroheteroaryl salts, N-nitropyridinium hexafluorophosphate [12], Nnitropyrazole/boron trifluoride diethyletherate [13] and N-nitrocollidinium tetrafluoroborate [14], gave meta contents in excess of 3% so these systems, which also suffer from the disadvantage of expensive and complex reagents, do not merit further consideration. Other systems which gave >=3% meta-nitrotoluene include: nitronium tetrafluoroborate in sulfolane [15], N 2 O 5 /tetraethylammonium tetrafluoroborate in acetonitrile under anodic conditions [16], N 2 O 4 /tetraethylammonium tetrafluoroborate in acetonitrile under electrolytic conditions [17], tetra-n-butylammonium nitrate/trifluoroacetic anhydride in nitromethane [18], calcium nitrate in nitric acid [19], nitric acid/acetic anhydride in the presence of zeolite-beta and a solvent [20], and anhydrous vanadium nitrate in dichloromethane [21]. In the following cases the proportion of meta isomer was not reported (thus presumed not to be notably low): ceric ammonium nitrate/trifluoroacetic acid (3 day reaction) [22], methyl nitrate under radiolysis [23], nitryl chloride in aqueous trifluoroacetic acid [24], N 2 O 4 -oxygen in 1,2-dichloroethane in the presence of zeolite beta [25] and ammonium nitrate/trifluoroacetic anhydride in the ionic liquid emim trifluoroacetate [26].…”

Section: Toluene Nitration -Initial Stagesmentioning

confidence: 99%

Annual Industrial Capabilities Report to Congress

Farnborough¹

2008

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The US Department of Defense requires an environmentally benign synthesis route for the manufacture of military grade trinitrotoluene (TNT) which eliminates the production of redwater arising from the sulfiting process for removing unsymmetrical trinitrotoluene isomers. QinetiQ has found that by using a novel nitrating system, N2O5 in dichloromethane, the proportion of meta-substituted nitrotoluenes can be reduced to 1.3-1.5%, instead of the 4-5% levels in current processes. Additional improvements have been made to the following di-and tri-nitration steps by using alternatives to traditional mixed (sulfuric-nitric) acid systems, namely 100% nitric acid and N2O5-sulfuric acid respectively, resulting in reduced emissions of pollutants (NOx offgas and tetranitromethane). As a result, TNT with a set point within 0.3 deg. C of the Mil. Spec. (80.2 deg. C) can be made by the QinetiQ process, without the need for sulfite washing; one recrystallization raises this figure to 80.6 deg. C. A study of the process economics has shown that the cost (at 4.5 million lb per annum scale) is not disproportionately greater than current processes.

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“…The reaction of acyl halides with organotin compounds, although sometimes possible without a catalyst, usually necessitates the addition of Lewis acids or ammonium salts to afford finally ketones via acyl cations 446 . However, in this field organosilicon derivatives are good rivals and a more interesting method of activation involves catalysis by transition metal complexes.…”

Section: Generalmentioning

confidence: 99%

“…The alkynylation reaction can occur on simple heating (without catalyst), but the reaction is more easily performed when activated by Lewis acids 446 Other examples reported with alkoxyalkynyltin derivatives 470 ' 471 show that the procedure is a valuable means of access to alkoxyethynyl ketones (Scheme 10.79 Similarly an extensive series of aminoethynyl ketones has been obtained, often in high yield, from stannyl ynamines by reacting either acyl chlorides or anhydrides 472 ' 473 (Scheme 10.80).…”

Section: Alkynylationmentioning

confidence: 99%