H2O2 - Urea/Phthalic Anhydride System - Convenient Reagent for the Mild and Efficient Preparation of Sulfones from Organic Sulfides

Balicki, R.; Kaczmarek, Ł.; Nantka-Namirski, P

doi:10.1002/prac.19933350218

Cited by 11 publications

(3 citation statements)

References 6 publications

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“…We also demonstrated one‐pot Julia–Kocienski olefination for two cases (X = H, Me) for comparison with double elimination of the original Julia olefination (entries 1 and 2). Allylic BT‐sulfones 8 were prepared in 60 % yield (X = H) and 75 % yield (X = Me) by sufurylation of 2‐mercaptobenzothiazole in acetone with K 2 CO 3 as base, followed by sulfur oxidation using mono peroxyphthalic acid, generated in situ by the reaction of urea‐H 2 O 2 (UHP) and phthalic anhydride in MeCN Allylic BT‐sulfones 8 were consisted of a 3–4:1 mixture of E/Z ‐isomers, but the E ‐form can be easily purified by trituration with MeOH.…”

Section: Resultsmentioning

confidence: 99%

Synthetic Strategy for Tetraphenyl‐Substituted All‐E‐Carotenoids with Improved Molecular Properties

et al. 2020

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The synthetic method of tetraphenyl‐substituted all‐E‐carotenes 1 with improved properties of antioxidant and molecular electronic conductance was developed through the formation of tetraphenyl‐substituted all‐E‐apocarotenedial 4. The synthesis highlighted the preparation of novel subunits containing phenyl substituent(s) with E‐configuration starting from the key (E)‐4‐chloro‐2‐phenylbut‐2‐enal (10), utilizing conjugation effect with formyl group or easy recrystallization of sulfone compounds. Sulfone‐mediated coupling methods of Julia and modified Julia–Kocienski olefinations utilizing the subunits were demonstrated to produce tetraphenyl‐substituted apocarotenedials 4. The major all‐E‐forms (73–85 % selectivity) were easily purified by SiO2 chromatography and trituration with Et2O due to the presence of the polar formyl groups. The olefination of all‐E‐apocarotenedials 4 and Wittig salt 5 provided all‐E‐9,9',13,13'‐tetraphenylcarotenes 1.

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Section: Resultsmentioning

confidence: 99%

Synthetic Strategy for Tetraphenyl‐Substituted All‐E‐Carotenoids with Improved Molecular Properties

et al. 2020

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“…agent than previously reported for oxidation in acetonitrile. 12 Herein we describe sulfide oxidation conditions with UHP and phthalic anhydride that apply to sulfides containing a variety of functional groups, are easy to use on a large scale, and provide high-purity sulfones, in most cases without additional purification.…”

Section: Syn Thesismentioning

confidence: 99%

An Efficient Oxidation of Sulfides to Sulfones with Urea–Hydrogen Peroxide in the Presence of Phthalic Anhydride in Ethyl Acetate

Lutz

Likhotvorik

2018

Synthesis

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“…The best yield of 40% was obtained by the oxidation with monoperphthalic acid that was generated in situ by the reaction of phthalic anhydride and a ureaÀH 2 O 2 complex in Me 3 CN [14].…”

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confidence: 99%

Allylic Sulfones Containing Triene Moieties as Key Synthons for Carotenoid Synthesis

Choi

Jeong

et al. 2003

Helvetica Chimica Acta

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An efficient synthetic method for the allylic sulfone 2 containing a conjugated triene moiety has been proposed involving i) coupling of allylic sulfones 4 with the C 5 bromoallylic sulfide 5, ii) base-promoted dehydrosulfonation in the presence of allylic sulfide, and iii) selective oxidation of the resulting trienyl sulfide to the corresponding sulfone. Total synthesis of lycopene starting from the C 15 allylic sulfone 2b has been described, where the new C 10 bis(chloroallylic) sulfone 11 proved to be a useful substitute for the C 10 bis(chloroallylic) sulfide 3, which did not require the problematic chemoselective sulfur oxidation in a conjugated polyene.Introduction. ± Carotenoids such as b-carotene (1a) and lycopene (1b) are characterized by long conjugated polyene chains that show distinctive red colors and are ideally utilized as nonhazardous dyes for foodstuffs. High reactivity of these polyenes with activated carcinogenic oxygen or radicals provides carotenoids with prophylactic effects against certain cancers of the pancreas, the mouth, and the bladder, etc.[1]. Among the numerous approaches that have appeared in the literature to build the conjugated polyene chains of carotenoids [2], methods based on acetylide coupling/ partial hydrogenation [3] and Wittig olefination [4] have been the two main synthetic approaches. The Julia sulfone olefination protocol [5], which has been applied to retinol synthesis [6], is presumed to be the best method to produce double bonds with the (E)-configuration [7]. We have introduced the C 10 bis(chloroallylic) sulfide 3 as a stable substitute for the highly unstable 1,8-dichloro-2,7-dimethylocta-2,4,6-triene, and successfully accomplished total syntheses of b-carotene (1a) and lycopene (1b) based on the Julia sulfone-olefination protocol [8]. To generalize this process with C 10 bis(chloroallylic) sulfide 3 for carotenoid syntheses, an efficient method should be devised to build allylic sulfones containing conjugated CC bonds such as 2 (Scheme 1). We herein report our strategy to synthesize allylic sulfones comprising a conjugated triene moiety and total synthesis of lycopene [9] by means of the allylic sulfone 2b.

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H2O2 - Urea/Phthalic Anhydride System - Convenient Reagent for the Mild and Efficient Preparation of Sulfones from Organic Sulfides

Cited by 11 publications

References 6 publications

Synthetic Strategy for Tetraphenyl‐Substituted All‐E‐Carotenoids with Improved Molecular Properties

Synthetic Strategy for Tetraphenyl‐Substituted All‐E‐Carotenoids with Improved Molecular Properties

An Efficient Oxidation of Sulfides to Sulfones with Urea–Hydrogen Peroxide in the Presence of Phthalic Anhydride in Ethyl Acetate

Allylic Sulfones Containing Triene Moieties as Key Synthons for Carotenoid Synthesis

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