Allylic Chlorides. X. Configuration of the 3-Chloro-2-buten-1-ols and the 1,3-Dichloro-2-butenes

Hatch, Lewis F.; Hudson, P.S.

doi:10.1021/ja01162a044

Cited by 8 publications

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“…The boiling points of ketone A (123°C/740 mm Hg [24]) and alkene 8 ( Z ‐8 128°C/745 mm Hg, E ‐8 131°C/748 mm Hg [25]) are close, so that they cannot be separated by distillation. Pretreatment of 1,3‐DCB with triethylamine at room temperature leads to the conversion of ketone A to ketone B .…”

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confidence: 99%

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[3 + 2] Cycloaddition of nitrile oxides to dichloropropenes and 1,3‐dichlorobut‐2‐ene: A regioselectivity issue

Shilova,

Shatokhina,

Kondrashov

2024

Journal of Heterocyclic Chem

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The reaction of nitrile oxides with 2,3‐dichloroprop‐1‐ene, 1,3‐dichloroprop‐1‐ene, and 1,3‐dichlorobut‐2‐ene leads to 5‐(chloromethyl)isoxazoles, 4‐(chloromethyl)isoxazoles, or to mixtures of both regioisomers. The direction of cycloaddition and reactivity of substrate is determined by the steric hindrance at the terminal carbon atom of the alkene double bond. It has been found that the isomeric products of cycloaddition of nitrile oxides to 1,3‐dichloropropene have significantly different dehydrochlorination capabilities. The experimental data on the regioselectivity of cycloaddition and the relative reactivity of substrates are in agreement with the results of quantum chemical calculations.

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confidence: 99%

“…IR (film), ν, cm À1 606, 836, 1179, 1259, 1515, 1608, 2839, 2961. MS: m/z (%) = 259 (100) [M] + , 210(20), 174(12), 155(45), 149 (92), 132(19), 115(20), 106(17), 92(20), 77(47), 63(25), 39(15). C 11 H 11 Cl 2 NO 2 .…”

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[3 + 2] Cycloaddition of nitrile oxides to dichloropropenes and 1,3‐dichlorobut‐2‐ene: A regioselectivity issue

Shilova,

Shatokhina,

Kondrashov

2024

Journal of Heterocyclic Chem

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“…3,4,6,7 tetracarboxylic anhydride (IX). The maleic anhydride adds first to one of the conjugated diene systems to form the intermediate monoadduct VIII.The two remaining double bonds are still in conjugation and add the second mole of dienophile.…”

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confidence: 99%