Dimerisation and oligomerisation by dehydrogenation as a general synthetic principle (1) part I

Naarmann, H.; Beaujean, M.; Mer�nyi, Robert; Viehe, H. G.

doi:10.1007/bf01064366

Cited by 20 publications

(8 citation statements)

References 31 publications

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“…One was a mixture of deuterated and undeuterated 2 (85 mg): MS, mje 141 (2), 140 (11), 139 (5.5), 138 (33), 104 (14), 103 (100). The other component was a mixture of deuterated and undeuterated 3 (195 mg): MS, mfz 175 (7.02), 174 (3.2), 104 (12), 103 (15), 92 (8.4), 91 (100).…”

Section: Methodsmentioning

confidence: 99%

Reaction of benzylchlorocarbene with hydrogen chloride

Liu¹,

Subramanian²

1985

J. Org. Chem.

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Section: Methodsmentioning

confidence: 99%

Reaction of benzylchlorocarbene with hydrogen chloride

Liu¹,

Subramanian²

1985

J. Org. Chem.

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“…For example, methyl crmethoxyacetate (c = COzMe, d = OMe) leads to the dimer of the captodative radical 57 in 91'% yield upon reaction with t-butyl peroxide [38]. This reaction can be extended, under certain conditions, to yield polymers with interesting properties [ 391.…”

Section: Dehydrodimerization and Polymerizationmentioning

confidence: 99%

Synthetic Utility of the Captodative Effect

Stella¹,

Harvey²

2001

Radicals in Organic Synthesis

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“…This reactive radical scavenging ability of NHPI may be responsible for the good selectivity of the discovered process. It is known that thermolysis of di- tert -butylperoxide in i -PrCOOMe (analogue of i -PrCOOEt) leads to its C-C dehydrogenative dimerization − and telomerization of i -PrCOOMe.…”

Section: Resultsmentioning

confidence: 99%

Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature

et al. 2019

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Cross-dehydrogenative C−O coupling of N-hydroxyimides with ketones, esters, and carboxylic acids was achieved employing the di-tertbutyl peroxide as a source of free radicals and a dehydrogenating agent. The proposed method is experimentally simple and demonstrates the outstanding efficiency for the challenging CH substrates, such as unactivated esters and carboxylic acids. It was shown that N-hydroxyphthalimide drastically affects the oxidative properties of t-BuOOt-Bu by intercepting the t-BuO • radicals with the formation of phthalimide-N-oxyl radicals, a species responsible for both hydrogen atom abstraction from the CH reagent and the selective formation of the C−O coupling product by selective radical cross-recombination. The practical applicability of the developed method was exemplified by the single-stage synthesis of commercial reagent (known as Baran aminating reagent precursor) from isobutyric acid and N-hydroxysuccinimide, whereas in the standard synthetic approach, four stages are necessary.

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Dimerisation and oligomerisation by dehydrogenation as a general synthetic principle (1) part I

Cited by 20 publications

References 31 publications

Reaction of benzylchlorocarbene with hydrogen chloride

Reaction of benzylchlorocarbene with hydrogen chloride

Synthetic Utility of the Captodative Effect

Metal-Free Cross-Dehydrogenative C–O Coupling of Carbonyl Compounds with N-Hydroxyimides: Unexpected Selective Behavior of Highly Reactive Free Radicals at an Elevated Temperature

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