Diels–Alder reactions of 4,4-dimethyl-2-cyclohexenones. A direct route to the 4,4-dimethyl-1-decalones

1987 ◽  
Vol 65 (6) ◽  
pp. 1262-1278 ◽  
Author(s):  
Hsing-Jang Liu ◽  
Eric N. C. Browne
Keyword(s):  
Magnetic Resonance ◽  
Transition States ◽  
Alder Reaction ◽  
Diels Alder ◽  
Steric Effects ◽  
Reaction Products ◽  
Direct Route ◽  
Diels Alder Reaction ◽  
Chemical Techniques ◽  
Electronic And Steric Effects

Diels–Alder additions to enones 1 and 2, synthetic equivalents of the synthon 3, were studied using a variety of hydrocarbon dienes. The two enones have been shown to be effective and synthetically useful dienophiles. Spectroscopic (especially 1H and 13C magnetic resonance) and chemical techniques were used to define unambiguously the full structures of the adducts. The structures of the various reaction products were used to draw qualitative conclusions about the nature of the transition states involved and the various electronic and steric effects that play a role in the mechanistic course of the Diels–Alder reaction.

ChemInform Abstract: Electronic and Steric Effects of Lewis Acidic Organoaluminum Reagents in the Diels-Alder Reaction.

ChemInform ◽  
1989 ◽  
Vol 20 (13) ◽  
Author(s):  
K. MARUOKA ◽  
K. NONOSHITA ◽  
H. YAMAMOTO
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Steric Effects ◽  
Diels Alder Reaction ◽  
Electronic And Steric Effects

Electronic and Steric Effects of Lewis Acidic Organoaluminum Reagents in the Diels-Alder Reaction

1988 ◽  
Vol 18 (13) ◽  
pp. 1453-1459 ◽  
Author(s):  
Keiji Maruoka ◽  
Katsumasa Nonoshita ◽  
Hisashi Yamamoto
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Steric Effects ◽  
Diels Alder Reaction ◽  
Electronic And Steric Effects

Asymmetric Synthesis of P-Chiral Diphosphines. Steric Effects on the Palladium-Complex-Promoted Asymmetric Diels−Alder Reaction between a Dimethylphenylphosphole and (E/Z)-Methyl-Substituted Diphenylvinylphosphines

1997 ◽  
Vol 36 (10) ◽  
pp. 2138-2146 ◽  
Author(s):  
Beng-Hwee Aw ◽  
T. S. Andy Hor ◽  
S. Selvaratnam ◽  
K. F. Mok ◽  
Andrew J. P. White ◽  
...  
Keyword(s):  
Asymmetric Synthesis ◽  
Palladium Complex ◽  
Alder Reaction ◽  
Diels Alder ◽  
Steric Effects ◽  
Diels Alder Reaction

scholarly journals Separation of Diels-Alder Reaction Products of 1, 3-p-Menthadiene with Methyl Acrylate and Fragrance of Their Derivatives

1971 ◽  
Vol 74 (10) ◽  
pp. 2097-2099
Author(s):  
Yoshiharu MATSUBARA ◽  
Takao KISHIMOTO ◽  
Yoshihiro MORICHIKA ◽  
Wasaku MINEMATSU
Keyword(s):  
Methyl Acrylate ◽  
Alder Reaction ◽  
Diels Alder ◽  
Reaction Products ◽  
Diels Alder Reaction

ChemInform Abstract: Structures of the Diels-Alder Reaction Products of Thymoquinone and 1- Vinylcyclohexene. Part 2. 7-Isopropyl-4-methyltricyclo(8.4.0.02,7) tetradeca-4,9-diene-3,6-dione, C18H24O2.

ChemInform ◽  
2010 ◽  
Vol 25 (16) ◽  
pp. no-no
Author(s):  
J. IULEK ◽  
J. ZUKERMAN-SCHPECTOR ◽  
T. J. BROCKSOM ◽  
F. JUN. SILVA
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Reaction Products ◽  
Diels Alder Reaction

Organic transition states. V. The Diels-Alder reaction

1976 ◽  
Vol 98 (8) ◽  
pp. 2190-2198 ◽  
Author(s):  
R. E. Townshend ◽  
G. Ramunni ◽  
G. Segal ◽  
W. J. Hehre ◽  
L. Salem
Keyword(s):  
Transition States ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Organic Transition

QTAIM–DI–VISAB computational study on the Diels–Alder reaction of cyclopentadiene — On the nature of the so-called secondary orbital interactions

2008 ◽  
Vol 86 (7) ◽  
pp. 737-744 ◽  
Author(s):  
Nick Henry Werstiuk ◽  
Wojciech Sokol
Keyword(s):  
Computational Study ◽  
Transition States ◽  
Alder Reaction ◽  
Diels Alder ◽  
Physical Organic Chemistry ◽  
Hydrogen Atoms ◽  
Endo Isomer ◽  
Orbital Interactions ◽  
Physical Organic ◽  
Diels Alder Reaction

We have undertaken a QTAIM–DI–VISAB computational study of the dimerization of cyclopentadiene (1), the archetypal example of a Diels–Alder reaction that has been studied experimentally and computationally. Secondary orbital interactions (SOIs) that have gained acceptance in the interpretation of stereoselectivities seen in many cycloaddition reactions have been used to account for the fact that the endo isomer was the kinetic product of the reaction. To this point, “classical” MO analyses along with a variety of arbitrarily assigned solid and dashed lines (solid lines and bold dashes for “primary” interactions and dashed and dotted lines to differentiate between different SOI schemes) have been used in an attempt to describe the bonding of the transition states. Yet, the existence of SOIs has been challenged. Our interest in applying QTAIM to fundamental chemical problems in physical organic chemistry, with the goal of refining our knowledge of the bonding in transition-states and ground-state molecules while obviating the need to use a variety of confusing arbitrarily assigned dashed and dotted lines, led us to a QTAIM–DI–VISAB computational study of the endo and exo dimerizations of 1 at the DFT B3PW91 and MPW1PW91 levels. We have characterized the bonding interactions between cyclopentadiene rings in the various transition states and show that “normal” bonds are present where SOIs have been considered to exist. There is no need to use different types of dashed and dotted lines. An analysis of the changes in atom energies revealed that the significant destabilization of the carbon atoms in achieving the TSs (potentially leading to a very high barrier) is ameliorated by a stabilization of the hydrogen atoms leading to the relatively low barrier for the D–A reaction.Key words: cyclopentadiene dimerization, bispericyclic transition states, DFT calculations, QTAIM–DI–VISAB analysis, bonding, atom energy analysis.

ChemInform Abstract: STEREOCHEMISTRY OF THE DIELS-ALDER REACTION, STERIC EFFECTS OF THE DIENOPHILE ON ENDO-SELECTIVITY

1974 ◽  
Vol 5 (12) ◽  
pp. no-no
Author(s):  
JOHN M. MELLOR ◽  
COLIN F. WEBB
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Steric Effects ◽  
Diels Alder Reaction
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