Cyclization of arylacetoacetates to indene and dihydronaphthalene derivatives in strong acids. Evidence for involvement of further protonation of O,O-diprotonated β-ketoester, leading to enhancement of cyclization

Journal of the American Chemical Society

Volumn 132, Issue 2, 2010, Pages 807-815

  Kurouchi, Hiroaki ^a   Sugimoto, Hiromichi ^a   Otani, Yuko ^a   Ohwada, Tomohiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ACETOACETATES; ACID-BASE TITRATION; AROMATIC RINGS; CATIONIC SPECIES; CHEMICAL FEATURES; CYCLIZATION REACTIONS; EFFICIENT METHOD; ELECTRONWITHDRAWING; ELECTROPHILICITY; FIVE-MEMBERED RINGS; KETO ESTER; NMR SPECTROSCOPY; PRODUCT DISTRIBUTIONS; PROTONATED; REACTION MECHANISM; REACTIVE INTERMEDIATE; STRONG ACIDS; SUPERACID; THERMOCHEMICAL DATA;

ACIDS; ACTIVATION ENERGY; CHEMICAL STABILITY; ESTERIFICATION; ESTERS; FUNCTIONAL GROUPS; KETONES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTONATION; TITRATION;

CYCLIZATION;

3,4 DIHYDRONAPTHALENE DERIVATIVE; ACETIC ACID DERIVATIVE; ARYLACETOACETATE DERIVATIVE; BETA OXOCARBOXYLIC ACID ESTER; ESTER DERIVATIVE; INDENE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CONTROLLED STUDY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON TRANSPORT; TITRIMETRY;

ACETOACETATES; CYCLIZATION; ESTERS; INDENES; MOLECULAR STRUCTURE; NAPHTHALENES; PROTONS; STEREOISOMERISM; SULFURIC ACIDS;

EID: 74949095911     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja908749u     Document Type: Article

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