Carbolithiation of aromatic rings: Cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines

Jonathan Clayden; Yann J Y Foricher; Ho Kam Lam

doi:10.1039/b206479k

Carbolithiation of aromatic rings: Cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines

Jonathan Clayden, Yann J Y Foricher, Ho Kam Lam

Research output: Contribution to journal › Article › peer-review

Abstract

Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.

Original language	English
Pages (from-to)	2138-2139
Number of pages	1
Journal	Chemical Communications
Issue number	18
DOIs	https://doi.org/10.1039/b206479k
Publication status	Published - 2002

Keywords

Amides Role: RCT (Reactant), RACT (Reactant or reagent) (N-aroyltetramethylpiperidines; prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines); Lithiation (carbo-, regioselective, stereoselective; prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines); Aromatization (de-; of N-aroyltetramethylpiperidines by alkyllithiums); Regiochemistry; Stereochemistry; Stereoselective synthesis (prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines)

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title = "Carbolithiation of aromatic rings: Cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines",

abstract = "Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.",

keywords = "Amides Role: RCT (Reactant), RACT (Reactant or reagent) (N-aroyltetramethylpiperidines; prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines); Lithiation (carbo-, regioselective, stereoselective; prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines); Aromatization (de-; of N-aroyltetramethylpiperidines by alkyllithiums); Regiochemistry; Stereochemistry; Stereoselective synthesis (prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines)",

author = "Jonathan Clayden and Foricher, {Yann J Y} and Lam, {Ho Kam}",

year = "2002",

doi = "10.1039/b206479k",

language = "English",

pages = "2138--2139",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "18",

}

TY - JOUR

T1 - Carbolithiation of aromatic rings: Cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines

AU - Clayden, Jonathan

AU - Foricher, Yann J Y

AU - Lam, Ho Kam

PY - 2002

Y1 - 2002

N2 - Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.

AB - Benzamides whose nitrogen atom is part of a 2,2,6,6-tetramethylpiperidine ring are dearomatised by alkyllithiums, which attack them regioselectively to yield, after electrophilic quench, substituted cyclohexadienes.

KW - Amides Role: RCT (Reactant), RACT (Reactant or reagent) (N-aroyltetramethylpiperidines; prepn. of cyclohexadienes by regioselective and stereoselective carbolithiation of N-aroyltetramethylpiperidines); Lithiation (carbo-, regioselective, stereoselective;

U2 - 10.1039/b206479k

DO - 10.1039/b206479k

M3 - Article

SN - 1359-7345

SP - 2138

EP - 2139

JO - Chemical Communications

JF - Chemical Communications

IS - 18

ER -

Carbolithiation of aromatic rings: Cyclohexadienes from N-aroyl-2,2,6,6-tetramethylpiperidines

Abstract

Keywords

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