A Rationale for the Ortho Effect in Electrophilic Aromatic Substitutions

Timothy Eckert; Grace Harmeyer; Steven Legate; Steven Mathe

doi:10.2174/1570178617666200207103755

A Rationale for the Ortho Effect in Electrophilic Aromatic Substitutions

Letters in Organic Chemistry ◽

10.2174/1570178617666200207103755 ◽

2020 ◽

Vol 17 (9) ◽

pp. 655-658

Author(s):

Timothy Eckert ◽

Grace Harmeyer ◽

Steven Legate ◽

Steven Mathe

Keyword(s):

Substituted Benzenes ◽

Ortho Effect

The ortho effect arises in certain electrophilic aromatic substitutions when a meta director is meta to an ortho/para director. Among the three expected isomer products, only the two isomers ortho to the meta director are produced normally. To find an explanation for the ortho effect, nitrations of two properly substituted benzenes were explored. Evidence supported an explanation based on resonance involving the meta director.

Download Full-text

Solvent effects in proton nuclear magnetic resonance spectra of substituted benzenes

Journal de Chimie Physique ◽

10.1051/jcp/1964610199 ◽

1964 ◽

Vol 61 ◽

pp. 199-203 ◽

Cited By ~ 11

Author(s):

P. Diehl

Keyword(s):

Nuclear Magnetic Resonance ◽

Magnetic Resonance ◽

Solvent Effects ◽

Proton Nuclear Magnetic Resonance ◽

Substituted Benzenes ◽

Nuclear Magnetic Resonance Spectra ◽

Magnetic Resonance Spectra ◽

Nuclear Magnetic

Download Full-text

Homocoupling of Substituted Benzenes to Symmetrical Biaryls with Mercury(II) in the Presence of Cerium(IV)

Journal of Chemical Research ◽

10.1177/174751989902300719 ◽

1999 ◽

Vol 23 (7) ◽

pp. 442-443

Author(s):

Nasser Iranpoor ◽

Marzieh Shekarriz

Keyword(s):

Substituted Benzenes ◽

High Yields

Homocoupling of substituted benzenes to symmetrical biaryls is achieved with different cerium(IV) compounds such as cerium(IV) triethylammonium nitrate (CTEAN), cerium(IV) pyridinium nitrate (CPN) and Ce(OTf)4 in the presence of HgII in good to high yields.

Download Full-text

A Highly PracticalInstantCatalyst for Cyclotrimerization of Alkynes to Substituted Benzenes

Organic Letters ◽

10.1021/ol0602295 ◽

2006 ◽

Vol 8 (7) ◽

pp. 1439-1442 ◽

Cited By ~ 77

Author(s):

Naoko Saino ◽

Fumihiro Amemiya ◽

Emi Tanabe ◽

Kouki Kase ◽

Sentaro Okamoto

Keyword(s):

Substituted Benzenes

Download Full-text

On the Lowest Triplet State of Substituted Benzenes. III. Optically Detected Magnetic Resonance Studies on the 3π π State of 1,2,4,5‐Tetrabromobenzene and 1,2,4,5‐Tetrachlorobenzene

The Journal of Chemical Physics ◽

10.1063/1.1678357 ◽

1972 ◽

Vol 57 (3) ◽

pp. 1050-1065 ◽

Cited By ~ 78

Author(s):

A. H. Francis ◽

C. B. Harris

Keyword(s):

Magnetic Resonance ◽

Triplet State ◽

Substituted Benzenes ◽

Magnetic Resonance Studies ◽

Optically Detected Magnetic Resonance ◽

Optically Detected ◽

Π State

Download Full-text

Empirical correlations in ultraviolet spectra of substituted benzenes. 1. Compounds with electron-withdrawing parent groups

The Journal of Organic Chemistry ◽

10.1021/jo00358a033 ◽

1986 ◽

Vol 51 (8) ◽

pp. 1336-1340 ◽

Cited By ~ 2

Author(s):

Edward J. Cowles

Keyword(s):

Empirical Correlations ◽

Substituted Benzenes ◽

Ultraviolet Spectra ◽

Parent Groups

Download Full-text

The ortho effect in directed C–H activation

Chemical Science ◽

10.1039/d1sc00642h ◽

2021 ◽

Author(s):

Balázs L. Tóth ◽

Anna Monory ◽

Orsolya Egyed ◽

Attila Domján ◽

Attila Bényei ◽

...

Keyword(s):

Transition Metal ◽

Steric Effects ◽

Ortho Effect ◽

Transition Metal Catalyzed ◽

Metal Catalyzed

The term and concept of Ortho Effect (OE) is introduced for the description of steric effects in transition metal catalyzed directed ortho C–H activation reactions to explain and predict reactivities of substrates.

Download Full-text