A Caveat Concerning Anionic Oxy-cope Rearrangements Within Bicyclo[2.2.2]octenyl Frameworks

1996 ◽  
Vol 49 (5) ◽  
pp. 639 ◽  
Author(s):  
MG Banwell ◽  
JR Dupuche ◽  
RW Gable
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction ◽  
Cope Rearrangements ◽  
Potassium Hydride

Compounds (10), (15) and (16) all react with potassium hydride at 0°C to give, via retro- Diels-Alder reaction, 1-methylnaphthalene (12) in 60-67% yield. No evidence could be obtained for the formation of a product derived from the anionic oxy-Cope rearrangement of substrate (16).

scholarly journals Synthesis of Complex Hexacyclic Compounds via a Tandem Rh(II)-Catalyzed Double-Cyclopropanation/Cope Rearrangement/Diels–Alder Reaction

2014 ◽  
Vol 16 (18) ◽  
pp. 4794-4797 ◽  
Author(s):  
Jillian E. Spangler ◽  
Yajing Lian ◽  
Sandeep N. Raikar ◽  
Huw M. L. Davies
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction

Regiochemical aspects of Diels-Alder reactions of cyclopentadienone

1977 ◽  
Vol 30 (10) ◽  
pp. 2307 ◽  
Author(s):  
MN Paddon-Row ◽  
HK Patney ◽  
RN Warrener
Keyword(s):  
Kinetic Parameters ◽  
Transition States ◽  
Alder Reaction ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction ◽  
Tentative Explanation

The regiochemistry of the Diels-Alder reaction between cyclopentadienone and 6,6-dimethylfulvene (isopropylidenecyclopentadiene) has been studied. Two adducts (in addition to cyclopentadienone dimer) were isolated and their structures were shown to be endo-10-isopropylidenetricyclo[5,2,1,02,6]-deca-4,8- dien-3-one (6a) and endo-3-isopropylidenetricyclo[5,2,1,02,6]deca-4,8- dien-10-one (7a). Kinetic parameters for the Cope rearrangement (6a) ↔ (7a) have been determined. The adducts (6a) and (7a) were formed in the ratio 45 : 55 respectively. Thus, in contrast to FMO predictions, and to its reaction with cyclopentadiene, cyclopentadienone tends to behave as a diene towards the fulvene. A tentative explanation of these results, based on angle strain in the transition states for the formation of Diels-Alder adducts, is proposed.

Cope Rearrangement versus a Novel Tandem Retro-Diels−Alder−Diels−Alder Reaction with Role Reversal†

2007 ◽  
Vol 9 (1) ◽  
pp. 113-115 ◽  
Author(s):  
Kuan-Jen Su ◽  
Jean-Luc Mieusset ◽  
Vladimir B. Arion ◽  
Lothar Brecker ◽  
Udo H. Brinker
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Role Reversal ◽  
Cope Rearrangement ◽  
Diels Alder Reaction

ChemInform Abstract: Hetero-Diels-Alder Reaction of Phosphinyl and Phosphonyl Nitroso Alkenes with Conjugated Dienes: An Aza-Cope Rearrangement.

ChemInform ◽  
2011 ◽  
Vol 42 (49) ◽  
pp. no-no
Author(s):  
Jesus M. de los Santos ◽  
Roberto Ignacio ◽  
Gloria Rubiales ◽  
Domitila Aparicio ◽  
Francisco Palacios
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction

Hetero-Diels–Alder Reaction of Phosphinyl and Phosphonyl Nitroso Alkenes with Conjugated Dienes: An Aza-Cope Rearrangement

2011 ◽  
Vol 76 (16) ◽  
pp. 6715-6725 ◽  
Author(s):  
Jesús M. de los Santos ◽  
Roberto Ignacio ◽  
Gloria Rubiales ◽  
Domitila Aparicio ◽  
Francisco Palacios
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Cope Rearrangement ◽  
Diels Alder Reaction
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