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

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

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).

Dihydrothiophenes.10. The preparation and Diels–Alder reactions of some sulfur and phosphorus-substituted dienophiles and 2-aza-substituted 1,3-dienes

1984 ◽  
Vol 62 (11) ◽  
pp. 2089-2093 ◽  
Author(s):  
John M. McIntosh ◽  
Lilianna Z. Pillon
Keyword(s):  
Thermal Decomposition ◽  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Diels Alder Reaction

The use of 3-carboxylated 2,5-dihydrothiophenes as the dienophilic component of the Diels–Alder reaction has been investigated. The yields are generally quite low. The formation of conjugated dienes that are aminated at an interior position of the conjugated chain by formation and thermal decomposition of 3-acetamido-2,5-dihydrothiophenes appears to be a viable route to these useful compounds. One example of the Diels–Alder reaction of 2-carboxylated diethyl vinylphosphonates is reported.

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

scholarly journals Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

2016 ◽  
Vol 12 ◽  
pp. 1949-1980 ◽  
Author(s):  
Lucie Brulíková ◽  
Aidan Harrison ◽  
Marvin J Miller ◽  
Jan Hlaváč
Keyword(s):  
Alder Reaction ◽  
Conjugated Dienes ◽  
Diels Alder ◽  
Conjugated Diene ◽  
Diels Alder Reaction ◽  
Oxazine Ring

The hetero-Diels–Alder reaction between a nitroso dienophile and a conjugated diene to give the 3,6-dihydro-2H-1,2-oxazine scaffold is useful for the synthesis of many biologically interesting molecules due to the diverse opportunities created by subsequent transformations of the resulting 1,2-oxazine ring. This review discusses the rationale for the observed regio- and stereoselectivity and the methods developed in recent years used to control and improve the stereo- and regioselectivity for the synthesis of 1,2-oxazine scaffolds.

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