Notes - The Reaction of Haloanisoles with Lithium Dimethylamide

Benkeser, Robert A.; Deboer, Charles Edwin

doi:10.1021/jo01109a602

Cited by 8 publications

(2 citation statements)

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“…13 A pioneering S N Ar-type amination reaction without activating groups was described by Benkeser and DeBoer in 1956, the treatment of anisole with preformed lithium dimethylamide gave the desired N,N-dimethylaniline, albeit in low yield (<10%). 14 Inspired by this work, Wynberg and co-workers found that lithium amides efficiently substitute…”

Section: Stoichiometric Base-promoted Aminationmentioning

confidence: 92%

Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)–O/C(sp2)–S Bond Cleavage Strategy

Long

Yang

et al. 2021

Synthesis

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Recently, intense efforts have been dedicated to the development of novel synthetic strategies to access aromatic amines due to their importance in the pharmaceuticals, agrochemicals, materials, and natural product areas. Although numerous transition-metal-catalyzed C–N formation strategies have been described for the preparation of aromatic amines in the past few decades, complementary methods under transition-metal-free conditions are still required. We present the recent advances in the exploration of innovative amination approaches via C(sp2)–O/C(sp2)–S bond cleavage in this review.1 Introduction2 Stoichiometric Base-Promoted Amination3 Base-Catalyzed Amination4 Photoredox-Catalyzed Amination5 Acid-Promoted Amination6 Conclusion and Perspectives

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Section: Stoichiometric Base-promoted Aminationmentioning

confidence: 92%

Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)–O/C(sp2)–S Bond Cleavage Strategy

Long

Yang

et al. 2021

Synthesis

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“…In addition, comparison of 5/4 product ratios for a particular halogen atom and a given molar excess of 3 indicates that reduction occurred to a greater extent with p-than with m-haloanisoles. For example, p-iodoanisole was converted to anisóle (5) in 35% yield whereas the corresponding meta isomer afforded 5 in 12% yield in the presence of a 2 M excess of 3.…”

mentioning

confidence: 99%

Investigation of the Mechanism of reductive dehalogenation of haloanisoles under aryne-forming conditions

Biehl¹,

LAPIS²,

Reeves³

1974

J. Org. Chem.

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Separation of the reductive dehalogenation mechanism proceeding via aryne (mechanism A) from direct halogen displacement mechanisms (mechanisms B and C) has been achieved. In the presence of large excesses of di-npropylamine as compared with lithium di-n-propylamide and haloanisole, aryne reduction is essentially eliminated. With the exception of o-and p-iodoanisole, haloanisole appears to undergo nonaryne reduction via mechanism B, hydride attack on ring halogen. Mechanism C, amide ion nucleophilic attack on ring halogen, most likely operates in the reduction of o-and p-iodoanisole. An explanation in terms of the influence of the methoxy group on (a) Results

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Chemical modification of Kevlar fiber surfaces and of model diamides

Tesoro

1986

J of Applied Polymer Sci

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SynopsisOrganic reactions of aromatic diamides as models for PF'TA fibers have been investigated to select reagents and conditions suitable for surface-controlled heterogeneous reactions on Kevlar filaments and fabrics. Amine functional groups have been incorporated into fiber surfaces by bromination followed by ammonolysis and by nitration followed by reduction. Modification of filaments has been attained without impairment of fiber properties. Preliminary experiments have also shown that the presence of amino groups on Kevlar fabric can provide remarkably improved peel strength and apparent interlaminar shear strength in epoxy laminates, suggesting a significant role of covalent bonding in improving adhesion in aramidepoxy composites.

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Notes - The Reaction of Haloanisoles with Lithium Dimethylamide

Cited by 8 publications

References 0 publications

Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)–O/C(sp2)–S Bond Cleavage Strategy

Recent Progress in Amination Enabled by Transition-Metal-Free C(sp2)–O/C(sp2)–S Bond Cleavage Strategy

Investigation of the Mechanism of reductive dehalogenation of haloanisoles under aryne-forming conditions

Chemical modification of Kevlar fiber surfaces and of model diamides

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