716. Aspects of stereochemistry. Part XVII. Oxetans from monoarenesulphonyl esters of 1,3-diols

Henbest, H. B.; Millward, B. B.

doi:10.1039/jr9600003575

Cited by 28 publications

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“…Moreover, the experimental procedure is very easy, rapid and robust. As we have this equipment in our laboratory, we conducted these Fries rearrangements in a domestic microwave oven …”

Section: Synthesis and Discussionmentioning

confidence: 99%

The quest for odorants having salicylate notes

Gaudin¹

2013

Flavour & Fragrance J

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We describe the synthesis and sensory characterization of a series of compounds which we anticipated would possess the olfactory notes of salicylates. We explored carba‐analogues, cyclic β‐keto esters and cyclic β‐diketones as salicylate analogues. Applying the simple concept of three‐dimensional structure similarity was very fruitful. Salicylate carba‐analogues and β‐keto esters, especially compounds 5, 7 and 10 for the first series and 27 and 28 for the second series, proved to be the most interesting type of compounds. For example, 1‐(2‐hydroxyphenyl)‐3‐phenyl‐1‐propanone (10), which can be found in nature, is nicely diffusive and has an excellent olfactory profile with an interesting dual floral–animal note. In general, these compounds may offer a first credible alternative to the popular salicylates. Copyright © 2013 John Wiley & Sons, Ltd.

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“…Moreover, the experimental procedure is very easy, rapid and robust. As we have this equipment in our laboratory, we conducted these Fries rearrangements in a domestic microwave oven …”

Section: Synthesis and Discussionmentioning

confidence: 99%

The quest for odorants having salicylate notes

Gaudin¹

2013

Flavour & Fragrance J

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“…5-tosyl)-~-xylose mit Natriummethoxid in Methanol ausschliesslich ein Oxetan (1,2-Isopropyliden-3,5-anhydro-~xylose) [ZO]. Henbest & MiZZward [21] erhielten aus cis-2-Hydroxymethyl-cyclohexanolen nur das Ringschlussprodukt, wahrend sie beim Isomeren mit trans-standigem Substituenten (trans-periplanare Anordnung) Fragmentierung (vgl. 1221) feststellten.…”

Section: A)unclassified

2β, 13‐Oxido‐apotrichothecane: Synthese, chemische und physikalische Eigenschaften. Verrucarine und Roridine, 23. Mitteilung

Schumacher

Gutzwiller

Tamm

1971

Helvetica Chimica Acta

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355,260) Bcr. C 47,33 H 3,97 N 3,9404 Gcf. C 47,34 H 4,23 N 3,81% Finanziclle Unterstiitzung verttanltcn wir den1 Schweiz. Nationutfonds. LITERATURVERZETCHNI S 111 (13. WIT. 71)S'ummuvy. Starting from the 12,13-epoxy-trichothecancs roridin C (trichodermol) (l), verrucarol (15) and trichothccolone (25), the isomeric 2~,13-epoxp-apotrichothecancs 9, 20 and 33 have been synthcsized. I n these compounds the oxetanc group proved t o be unexpectedly stable to mincral acids and complex metal hydrides, probably due t o its fusion t o a cyclopentanc ring. Thc I R . and NMR. spectra of the oxetanes are discussed.

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“…Reactions of y-halohydrins (or 1,3-diols) or their esters with aqu~ous potassium hydroxide 3 • 4 or potassium tert-butoxide 5 are often used in the synthesi~ of oxetanes. Compounds I can be looked upon as r-chlorohydrins, as well as ~-chloro ethers, the latter suggesting that the chlorine atom will resist considerably a nucleophilic substitution 6 • In actual fact, reaction of both alcohols I and esters II with aqueous potassium hydroxide at 373 K afforded products of hydrolysis and/or elimination in about 80% yields and it was not possible to prove the formation of the corresponding oxetanes.…”

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Prototropic rearrangement in reactions of 4-alkoxy-3-chloro-1-butanols with bases

Poisel¹,

Krejča²,

Jonas³

1978

Collect. Czech. Chem. Commun.

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Reaction of 4-alkoxy-2-chloro-l-butanols (1) and their acetates II with bases depends on the base and reaction conditions employed and affords complex mixtures of fragmentation products or mixtures of 4-alkoxy-2-buten-l-ols (III) and 4-alkoxy-3-buten-l-ols (IV) or almost pure trans-IV. Hydrogenolysis of 2,5-dihydro-2,5-dimethoxyfuran (V) by chloroalane leads to trans--4-methoxy-2-buten-l-ol (trans-IlIa). Vinyl ethers IV undergo an acid-catalyzed cycIisation to the corresponding 2-alkoxytetrahydrofurans VI.We have described 1 a simple method which affords high yields of 4-alkoxy-3-chloro--l-butanols (1) and their acetates 2 II. The present communication describes our studies of the behaviour of compounds I and II in their reactions with bases.Reactions of y-halohydrins (or 1,3-diols) or their esters with aqu~ous potassium hydroxide 3 • 4 or potassium tert-butoxide 5 are often used in the synthesi~ of oxetanes. Compounds I can be looked upon as r-chlorohydrins, as well as ~-chloro ethers, the latter suggesting that the chlorine atom will resist considerably a nucleophilic substitution 6 • In actual fact, reaction of both alcohols I and esters II with aqueous potassium hydroxide at 373 K afforded products of hydrolysis and/or elimination in about 80% yields and it was not possible to prove the formation of the corresponding oxetanes. The mixtures of elimination products were separated only on the anIytical scale using an efficient capillary column. We found that these mixtures consist invariably of four components, two of which represent about 85 -90% of the mixture and their ratio is 1 : 1 to 1 : 2 depending on the starting compound. The elementar analyses of the mixtures corresponded exactly to the values calculated for alkoxybutenols. Also their 1 H-NMR, spectra, simplified by working with hexadeuteriodimethyl sulfoxide solutions 7 and by using shift reagents, indicated that the main portions of the mixtures are always the corresponding trans-4-alkoxy-2-buten-l-ols (trans-III) together with trans-4-alkoxy-3-buten-l-ols (trans-IV). As shown in Table I, the 1 H-NMR studies involved the determination of the coupling constants between olefinic protons S and comparison of calculated 9 and found chemical shifts of these protons.

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716. Aspects of stereochemistry. Part XVII. Oxetans from monoarenesulphonyl esters of 1,3-diols

Cited by 28 publications

References 0 publications

The quest for odorants having salicylate notes

The quest for odorants having salicylate notes

2β, 13‐Oxido‐apotrichothecane: Synthese, chemische und physikalische Eigenschaften. Verrucarine und Roridine, 23. Mitteilung

Prototropic rearrangement in reactions of 4-alkoxy-3-chloro-1-butanols with bases

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