Tuning selectivity of anionic cyclizations: Competition between 5-exo and 6-endo-dig closures of hydrazides of o-acetylenyl benzoic acids and based-catalyzed fragmentation/recyclization of the initial 5-exo-dig products

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8106-8117

  Vasilevsky, Sergey F ^a   Mikhailovskaya, Tat'yana F ^a   Mamatyuk, Victor I ^b   Salnikov, Georgy E ^b   Bogdanchikov, Georgy A ^a,c   Manoharan, Mariappan ^d   Alabugin, Igor V ^a,e  

^a INSTITUTE OF CHEMICAL KINETICS AND COMBUSTION   (Russian Federation)

^b N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^c INSTITUTE OF COMPUTATIONAL MATHEMATICS AND MATHEMATICAL GEOPHYSICS   (Russian Federation)

^d BETHUNE COOKMAN UNIVERSITY   (United States)

^e FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNATIVE PATH; ANIONIC INTERMEDIATES; ANIONIC NITROGEN; BENCHMARK DATA; BENZOIC ACID; CARBANIONIC CENTERS; CHEMICAL EQUATIONS; CYCLIZATIONS; DFT COMPUTATIONS; DOMINO-CYCLIZATION; DRIVING FORCES; EXO-CYCLIZATION; EXOTHERMICITY; EXTERNAL CONDITIONS; FUTURE APPLICATIONS; KINETIC CONTROL; NEUTRAL SPECIES; NITROGEN HETEROCYCLES; NITROGEN NUCLEOPHILES; REACTION CONDITIONS; RELATIVE RATES; RELATIVE STABILITIES; RING OPENING; STEREOELECTRONIC EFFECT; TAUTOMERIZATIONS; TRIPLE BONDS;

ACETYLENE; ACIDS; AROMATIC HYDROCARBONS; COMPETITION; ELECTRON TRANSITIONS; ISOMERIZATION; ISOMERS; NEGATIVE IONS; NITROGEN; REACTION RATES; STEREOSELECTIVITY;

CYCLIZATION;

ALKYNE; ANION; BENZOIC ACID DERIVATIVE; HYDRAZIDE DERIVATIVE; NITROGEN; NUCLEOPHILE;

ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; CYCLIZATION; DENSITY FUNCTIONAL THEORY; DRUG SYNTHESIS; FRAGMENTATION REACTION; ISOMERIZATION; MOLECULAR INTERACTION; MOLECULAR STABILITY; RING OPENING; SENSITIVITY ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

AZIDES; BENZOIC ACIDS; CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 70350705891     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901551g     Document Type: Article

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