Nitrones and oxaziridines. XXI. Electronic substituent effects in nitrone cycloadditions to highly polarized alkenes

1,3-Dipolar cycloaddition reactions of nitrones-particularly N-(2'- pyridylmethylene)aniline N-oxide-with arylmethylene cyanoacetates exclusively yield 4,4-disubstituted isoxazolidines, identifiable by 1H n.m.r, spectroscopy and isolable in some cases. Comparative kinetic experiments provide evidence for at least non-synchronous addition via a dipolar intermediate or possibly even two-step addition via a discrete zwitterionic intermediate.

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1-3-Dipolar cycloaddition reactions of diazoalkanes. Part III. Substituent effects on the kinetics of reactions between diazomethane and some unsaturated esters

Journal of the Chemical Society B Physical Organic ◽

10.1039/j29670000083 ◽

1967 ◽

pp. 83 ◽

Cited By ~ 5

Author(s):

A. Ledwith ◽

Yang Shih-Lin

Keyword(s):

Substituent Effects ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Unsaturated Esters ◽

Kinetics Of

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Temperature andPara-Substituent Effects on the Face Selectivity of 1,3-Dipolar Cycloaddition Reactions of Benzonitrile Oxides with 5-Substituted Adamantane-2-thiones,N-Benzyladamantyl-2-imines, and 2-Methyleneadamantanes

The Journal of Organic Chemistry ◽

10.1021/jo980945n ◽

1999 ◽

Vol 64 (4) ◽

pp. 1099-1107 ◽

Cited By ~ 11

Author(s):

Tzong-Liang Tsai ◽

Wei-Cheng Chen ◽

Chin-Hui Yu ◽

W. J. le Noble ◽

Wen-Sheng Chung

Keyword(s):

Substituent Effects ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

The Face ◽

Face Selectivity

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ChemInform Abstract: Substituent Effects in the 1,3-Dipolar Cycloaddition Reactions of 2- Methylenecephalosporins with Diazoalkanes.

ChemInform ◽

10.1002/chin.199139252 ◽

2010 ◽

Vol 22 (39) ◽

pp. no-no

Author(s):

J. PITLIK ◽

J. C. JASZBERENYI ◽

I. KOMAROMI

Keyword(s):

Substituent Effects ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions

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Substituent effects in the 1,3-dipolar cycloaddition reactions of 2-methylenecephalosporins with diazoalkanes

Liebigs Annalen der Chemie ◽

10.1002/jlac.1991199101123 ◽

1991 ◽

Vol 1991 (7) ◽

pp. 699-701 ◽

Cited By ~ 3

Author(s):

János Pitlik ◽

J. Csaba Jászberényi ◽

István Komáromi

Keyword(s):

Substituent Effects ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions

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Multicomponent 1,3-Dipolar Cycloaddition Reactions in the Construction of Hybrid Spiroheterocycles

Current Organic Chemistry ◽

10.2174/13852728113179990091 ◽

2013 ◽

Vol 17 (18) ◽

pp. 1929-1956 ◽

Cited By ~ 16

Author(s):

Natarajan Arumugam ◽

Raju Kumar ◽

Abdulrahman Almansour ◽

Subbu Perumal

Keyword(s):

Dipolar Cycloaddition ◽

Cycloaddition Reactions

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Synthesis of New Aryl(Hetaryl)-Substituted Tandospirones Under Reductive Heck Type Hydroarylations and Isoxazoline Derivatives via 1,3-Dipolar Cycloaddition Reactions with Expected Anxiolytic Activity†

Current Organic Synthesis ◽

10.2174/1570179411310030010 ◽

2013 ◽

Vol 10 (3) ◽

pp. 481-485 ◽

Cited By ~ 2

Author(s):

Irem Kulu ◽

Asli Kopruceli ◽

Gokce Goksu ◽

Nuket Ocal

Keyword(s):

Anxiolytic Activity ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions

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π-Facial Selectivity in 1,3-Dipolar Cycloaddition Reactions of α-Methylidene-γ-lactone Substituted by 4-Methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl Group in γ-Position

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc20020353 ◽

2002 ◽

Vol 67 (3) ◽

pp. 353-364 ◽

Cited By ~ 3

Author(s):

Petr Melša ◽

Ctibor Mazal

Keyword(s):

Double Bond ◽

Carboxylic Acid ◽

Nitrile Oxide ◽

Dipolar Cycloaddition ◽

Cycloaddition Reactions ◽

Enantiomerically Pure ◽

Nitrile Imine ◽

Facial Selectivity ◽

Excellent Selectivity

Diastereoselectivity of 1,3-dipolar cycloaddition reactions of benzyl azide, diazomethane, a nitrile oxide and a nitrile imine to α-methylidene-γ-lactone dipolarophile was effectively controlled by a bulky γ-substituent, 4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl in γ-position of the dipolarophile. The dipoles added from the less hindered face of the double bond with an excellent selectivity. Enantiomerically pure dipolarophile was prepared from the easily available (S)-5-oxotetrahydrohydrofuran-2-carboxylic acid.

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