A high temperature investigation using microwave synthesis for electronically and sterically disfavoured substrates of the Newman–Kwart rearrangement

Moseley, Jonathan D.; Lenden, Philip

doi:10.1016/j.tet.2007.02.101

Cited by 47 publications

(27 citation statements)

References 35 publications

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“…This confirms that for these cases only bulk temperature effects are responsible for the observed enhancements and that the electromagnetic field has no direct influence on the reaction pathway (specific or nonthermal microwave effects) 3. 4 The results obtained for selected examples involving Mizoroki–Heck couplings,11 the alkylation of triphenylphosphine with benzyl chloride,5b and Newman–Kwart12, 13 and Claisen rearrangements7, 13, 14 are highlighted in Scheme . Additional case studies are presented in Scheme S1 in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

2009

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Section: Methodsmentioning

confidence: 99%

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

2009

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“…[3,4] The results obtained for selected examples involving Mizoroki-Heck couplings, [11] the alkylation of triphenylphosphine with benzyl chloride, [5b] and Newman-Kwart [12,13] and Claisen rearrangements [7,13,14] are highlighted in Scheme 1. This confirms that for these cases only bulk temperature effects are responsible for the observed enhancements and that the electromagnetic field has no direct influence on the reaction pathway (specific or nonthermal microwave effects).…”

Section: Methodsmentioning

confidence: 99%

“…This confirms that for these cases only bulk temperature effects are responsible for the observed enhancements and that the electromagnetic field has no direct influence on the reaction pathway (specific or nonthermal microwave effects). [3,4] The results obtained for selected examples involving Mizoroki-Heck couplings, [11] the alkylation of triphenylphosphine with benzyl chloride, [5b] and Newman-Kwart [12,13] and Claisen rearrangements [7,13,14] are highlighted in Scheme 1. Additional case studies are presented in Scheme S1 in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

2009

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Ölbadchemie unter Mikrowellenbestrahlung: In Reaktionsgefäßen aus Siliciumcarbid (SiC) können Experimente, wie sie in einem Autoklaven mit Wärmeübertragung ausgeführt würden, in einem Mikrowellenreaktor simuliert werden, weil das elektromagnetische Feld der Mikrowellen durch die SiC‐Gefäße effizient abgeschirmt wird. Dieses Verfahren ermöglicht es, den Einfluss von Mikrowelleneffekten zu studieren.

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“…NKR has been intensively investigated over the past decade [3] and several methodologies are reported. One can cite thermal, [4] microwave, [5] metal, [6] Lewis [7] or lightassisted. [8] Finally, the free thiophenol is obtained using LiAlH 4 or bases such as NaOH, KOH, MeONa or tBuOK.…”

Section: Introductionmentioning

confidence: 99%

Unexpected Migration and O to S Benzylic Shift of Thiocarbamate-containing Salicylaldehyde Derivatives.

et al. 2016

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An unexpected reactivity of the O-dimethylthiocarbamate function has been evidenced concomitantly with the reduction of an aldehyde function presents at its ortho (o-) position. A systematic study using various substrates showed the exclusive formation of the rearranged compounds after 24 h and confirmed that the only-reduced compounds are reaction intermediates. However, electronic/steric contributions of the aromatic ring substituents on the composition of the reaction mixture (reduction of the aldehyde vs. migration) were observed at the early stage of the reaction (2 h). These new benzyl S-thiocarbamates compounds could be of particular interest as precursors for not trivial and functionalized free methylthiobenzyl alcohols.

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A high temperature investigation using microwave synthesis for electronically and sterically disfavoured substrates of the Newman–Kwart rearrangement

Cited by 47 publications

References 35 publications

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

Microwave Chemistry in Silicon Carbide Reaction Vials: Separating Thermal from Nonthermal Effects

Unexpected Migration and O to S Benzylic Shift of Thiocarbamate-containing Salicylaldehyde Derivatives.

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