The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans

Most of this review article has been prepared during Covid 19 pandemy. Therefore, we dedicate it,-first to all persons who unfortunately died from this disease and,-second to all people (medical doctors and many others) who helped their congeners to survive to this pandemy. The Meyer-Schuster rearrangement is an efficient method to prepare α,β-unsatured carbonyl compounds starting from propargylic alcohols and this review presents the remarkable progress made during the last decade in this reaction. New efficient catalytic systems have been discovered and many elegant applications have been reported for this rearrangement. To be noticed in particular are the new and efficient cascade processes affording a wide range of carbo-and heterocyclic molecules. Moreover, brilliant applications of this rearrangement have been described as well, in the total synthesis of complex natural products and their analogues. Finally, the first examples of aza-Meyer-Schuster rearrangements have been recently described as well.

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“…The MSR has been used to prepare naphthols and photochromic naphtopyrans as indicated in Scheme 29 [77a,b] …”

Section: Cascade Reactions Starting By a Meyer Schuster Rearrangementmentioning

confidence: 99%

Recent Developments in the Meyer‐Schuster Rearrangement

Justaud¹,

Hachem

Grée³

2021

Eur J Org Chem

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“…The title compound was prepared according to general procedure C from (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-ol 75 (E)-1-(Allyloxy)-1-phenyl-3-(4-trifluoromethoxyphenyl)prop-2-ene (11e).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers

et al. 2015

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Two base-mediated cascade rearrangement reactions of diallyl ethers were developed leading to selective [2,3]-Wittig-oxy-Cope and isomerization-Claisen rearrangements. Both diaryl and arylsilyl-substituted 1,3-substituted propenyl substrates were examined, and each exhibits unique reactivity and different reaction pathways. Detailed mechanistic and computational analysis was conducted, which demonstrated that the role of the base and solvent was key to the reactivity and selectivity observed. Crossover experiments also suggest that these reactions proceed with a certain degree of dissociation, and the mechanistic pathway is highly complex with multiple competing routes.

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“…37 By 1 H NMR spectroscopy, it was determined that 1-H, which usually resonates as a doublet at ca. 7.3 ppm, 38 appeared upfield at 6.01 ppm as it was shielded by the induced anisotropic field from the pyridyl substituent at C-10.…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis and Photochromism of Novel Pyridyl-Substituted Naphthopyrans

et al. 2020

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Multi-target synthetic strategies to access novel photochromic 3H-naphtho[2,1b]pyrans decorated with pyridyl units are described. The new pyridyl substituted 3Hnaphtho[2,1-b]pyrans display good photochromic properties with the reversible generation of photomerocyanines which exhibit mainly orange/red hues. Photochromic parameters including photocolourability and persistence of colour vary tremendously on structural modification of the naphthopyran core.

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The influence of a 1,1-diarylvinyl moiety on the photochromism of naphthopyrans

Cited by 18 publications

References 33 publications

Recent Developments in the Meyer‐Schuster Rearrangement

Recent Developments in the Meyer‐Schuster Rearrangement

Base-Mediated Cascade Rearrangements of Aryl-Substituted Diallyl Ethers

Synthesis and Photochromism of Novel Pyridyl-Substituted Naphthopyrans

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