Vitamin C in organic synthesis: reaction with p-hydroxybenzyl alcohol derivatives

Poss, A. J.; Belter, Randolph K.

doi:10.1021/jo00242a037

Cited by 36 publications

(27 citation statements)

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“…The 4-hydroxymethyl groups in 2,4-DMMP were more reactive than the 2-hydroxymethyl groups in 2,6-DMMP, according to a previous paper. 23 Therefore, the crosslinking reaction of Noria-OEt with 2,4-DMMP proceeded more smoothly than that with 2,6-DMMP and quickly formed the resolution pattern during the lithography process.…”

Section: Protonated Benzyl Ethermentioning

confidence: 97%

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Niina

Kudo

Maruyama³

et al. 2011

Polym J

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The characteristics of Noria analogs with 12 ethoxy groups and 12 hydroxy groups (Noria-OEt), which were synthesized by the condensation reaction of 3-ethoxyphenol with 1,5-pentanedial, were examined in detail. The solubility of the synthesized Noria-OEt in common organic solvents was better than that of Noria. In addition, Noria-OEt was soluble in 2.38 wt% tetrametyl ammonium hydroxide (TMAH) aqueous as a developer. The thermal stability and mechanical properties were similar to those of Noria because of the ladder structure and amorphous characteristics, which means that the film-forming properties were confirmed. These characteristics are advantageous for use as a molecular glass photoresist. The patterning properties of the negative-type, alkaline developable, multicomponent photoresist based on Noria-OEt, with polyfunctional benzyl alcohols as a crosslinker and a photoacid generator, were evaluated with an extreme ultraviolet lithography system. This negative-type photoresist with 2,4-dihydroxymethyl-6-methylphenol as a crosslinker gave a resolution pattern of 35 nm half-pitch with 10.0 mJ cm À2 .

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Section: Protonated Benzyl Ethermentioning

confidence: 97%

Multicomponent negative-type photoresist based on Noria analog with 12 ethoxy groups

Niina

Kudo

Maruyama³

et al. 2011

Polym J

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“…Biomimetic syntheses of delesserine, methylrhodomelol and rhodomelol have been achieved by the Poss group in simple single step incubations of ascorbic acid or 2- O -methylascorbic acid with the corresponding p -hydroxybenzyl alcohol (Poss and Belter, 1988). These reactions undergo an S N 1 mechanism, and require the p -hydroxy group to stabilize the carbocation intermediate.…”

Section: Ascorbate As Nucleophilementioning

confidence: 99%

Covalent interaction of ascorbic acid with natural products

Kesinger

Stevens

2009

Phytochemistry

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While ascorbic acid (Vitamin C) is mostly known as a cofactor for proline hydroxylase and as a biological antioxidant, it also forms covalent bonds with natural products which we here refer to as 'ascorbylation'. A number of natural products containing an ascorbate moiety has been isolated and characterized from a variety of biological sources, ranging from marine algae to flowering plants. Most of these compounds are formed as a result of nucleophilic substitution or addition by ascorbate, e.g. the ascorbigens from Brassica species are ascorbylated indole derivatives. Some ascorbylated tannins appear to be formed from electrophilic addition to dehydroascorbic acid. There are also examples of annulations of ascorbate with dietary polyphenols, e.g., epigallocatechin gallate (EGCG) and resveratrol derivatives. Herein is a survey of thirty-three ascorbylated natural products and their reported biological activities.

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“…Ascorbate anions can react with quinonemethides formed upon the detachment of water from some 4-hydroxybenzyl alcohols 43 [52] or from 3-hydroxymethylindoles 44 [53] under the conditions of protonation in acid media (scheme 18). The products of such reactions are C-2-substituted derivatives (for example, 45a -45d), which include numerous natural alkaloids possessing biological activity.…”

Section: Reactions With Quinonemethides and Similar Compoundsmentioning

confidence: 99%

“…The products of such reactions are C-2-substituted derivatives (for example, 45a -45d), which include numerous natural alkaloids possessing biological activity. Examples are offered by delesserin 45b, rodomethol 45c, and methylrodomethol 45d (which were isolated from sea algae possessing anticoagulant properties [52]), ascorbigen 46 (isolated from plants of the Cruciferae family [53]), and others [52,44]. Properties of ascorbigen.…”

Section: Reactions With Quinonemethides and Similar Compoundsmentioning

confidence: 99%