Noncovalent Li···H Interaction in the Synthesis of peri-Disubstituted Naphthalene Proton Sponges

Noncovalent Li···H interaction was utilised as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of 1,8-bis(dimethylamino)naphthalene has been prepared in good to excellent yield after quenching the reaction mass with different electrophiles.

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Non-covalent Li···H interaction in the synthesis of peri-disubstituted naphthalene proton sponges.

10.3762/bxiv.2019.14.v1 ◽

2019 ◽

Author(s):

Alexander S Antonov

Keyword(s):

Reaction Mass ◽

Excellent Yield ◽

Proton Sponges ◽

Derivatives Of

Non-covalent Li···H interaction was utilized as a tool for the second lithiation of 4-lithio-1,8-bis(dimethylamino)naphthalene with n-BuLi in the presence of TMEDA in hexane. Metallation proceeds with 100% selectivity in the second peri-position and with up to 90% yield. A series of 4,5-disubstituted derivatives of DMAN has been prepared in a good to excellent yield after quenching the reaction mass with different electrophiles.

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10-Dimethylamino Derivatives of Benzo[h]quinoline and Benzo[h]quinazolines: Fluorescent Proton Sponge Analogues with Opposed peri-NMe2/–N═ Groups. How to Distinguish between Proton Sponges and Pseudo-Proton Sponges

The Journal of Organic Chemistry ◽

10.1021/acs.joc.6b00917 ◽

2016 ◽

Vol 81 (13) ◽

pp. 5574-5587 ◽

Cited By ~ 15

Author(s):

Alexander F. Pozharskii ◽

Valery A. Ozeryanskii ◽

Vladimir Y. Mikshiev ◽

Alexander S. Antonov ◽

Anatoly V. Chernyshev ◽

...

Keyword(s):

Proton Sponge ◽

Proton Sponges ◽

Derivatives Of

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Synthesis of New Arylsulfonylurea Derivatives of Saccharin

Australian Journal of Chemistry ◽

10.1071/ch9930903 ◽

1993 ◽

Vol 46 (6) ◽

pp. 903 ◽

Cited By ~ 1

Author(s):

M Benicha ◽

A Azmani ◽

M Akssira ◽

DT Hurst

Keyword(s):

Ethyl Chloroformate ◽

Excellent Yield ◽

Derivatives Of

Some new sulfonylurea derivatives (2a-j) of saccharin have been obtained by the reaction of ethyl 3-oxo-1,2-benzisothiazole-2(3H)-carboxylate 1,1-dioxide (1) with the appropriate amine. Ethyl 3-oxo-1,2-benzisothiazole-2(3H)-carboxylate 1,1-dioxide was obtained, in excellent yield, by the reaction of ethyl chloroformate with saccharin.

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The chemistry of aryllead tricarboxylates. Synthesis of some α-aryl α,β-unsaturated carbonyl compounds

Australian Journal of Chemistry ◽

10.1071/ch9830311 ◽

1983 ◽

Vol 36 (2) ◽

pp. 311 ◽

Cited By ~ 8

Author(s):

RP Kopinski ◽

JT Pinhey

Keyword(s):

Carbonyl Compounds ◽

Methyl Substituent ◽

Excellent Yield ◽

Derivatives Of

The treatment of 4-benzoyltetrahydrofuran-2,3-dione (2a) with 2 equiv. of phenyllead triacetate (3a) in chloroform gives 1,2-diphenylpropenone (4a) in excellent yield. This reaction has been investigated with a number of similar derivatives of tetrahydrofuran-2,3-dione and a number of aryllead triacetates. It has been found to be very sensitive to the nature of the substituent at C4, and it would appear to be limited to the synthesis of a-methylene carbonyl compounds since a 5-methyl substituent inhibits the reaction.

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