Dimerization of the quinone methide, 2,4-di-tert-butyl-6-ethylidene-2,5-cyclohexadien-1-one. Possible Diels-Alder mechanism

1969 ◽  
Vol 34 (1) ◽  
pp. 227-229 ◽  
Author(s):  
Clinton D. Cook ◽  
Leroy C. Butler
Keyword(s):  
Diels Alder ◽  
Quinone Methide ◽  
Tert Butyl

Asymmetric Synthesis of Fused Tetrahydroquinolines via Intramolecular Aza-Diels-Alder Reaction of ortho-Quinone Methide Imines

Synthesis ◽  
2021 ◽  
Author(s):  
Fabian Hofmann ◽  
Cornelius Gärtner ◽  
Martin Kretzschmar ◽  
Christoph Schneider
Keyword(s):  
Asymmetric Synthesis ◽  
Alder Reaction ◽  
Single Step ◽  
Diels Alder ◽  
Quinone Methide ◽  
Bronsted Acid ◽  
Atom Economy ◽  
Diels Alder Reaction ◽  
Brönsted Acid ◽  
Chiral Bronsted Acid

Aza-Diels Alder reactions are straightforward processes in the construction of N-heterocycles, featuring inherent atom-economy and stereospecificity. Intramolecular strategies allow formation of bicyclic core structures with up to three stereocenters within a single step. Herein, this concept is combined with the chemistry of chiral Brønsted acid-bound ortho-quinone methide imines generating a range of interesting fused tetrahydro-quinolines in a diastereo- and enantioselective manner.

A Flow Microreactor Approach to a Highly Efficient Diels–Alder Reaction with an Electrogenerated o-Quinone

Synlett ◽  
2019 ◽  
Vol 30 (10) ◽  
pp. 1194-1198 ◽  
Author(s):  
Kenta Tanaka ◽  
Hirona Yoshizawa ◽  
Mahito Atobe
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Tert Butyl ◽  
Highly Efficient ◽  
Diels Alder Reaction ◽  
Flow Microreactor ◽  
Chemical Oxidants

We have demonstrated a Diels–Alder reaction of an o-quinone generated in an electrochemical flow microreactor. In the flow microreactor system, 4-tert-butyl-o-benzoquinone was easily electrogenerated from 4-tert-butylpyrocatechol in the absence of chemical oxidants and then rapidly used, without decomposing, in a subsequent Diels–Adler reaction with various fulvenes to give the desired products efficiently.

One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o -quinone methide with unactivated dienes

Tetrahedron ◽  
2016 ◽  
Vol 72 (47) ◽  
pp. 7642-7649 ◽  
Author(s):  
Jian Liu ◽  
Xiaoxiao Wang ◽  
Lubin Xu ◽  
Zhihui Hao ◽  
Liang Wang ◽  
...  
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Quinone Methide ◽  
Inverse Electron Demand ◽  
Diels Alder Reaction ◽  
One Step ◽  
Electron Demand

Chiral Dienophiles Derived from Malic Acid: Synthesis of (Z)-(2S)-(tert-Butyl)-5-(ethoxycarbonylmethylene)-1,3-dioxolan-4-one and Its Diels-Alder Reaction with Cyclopentadiene

Synthesis ◽  
1990 ◽  
Vol 1990 (07) ◽  
pp. 599-603 ◽  
Author(s):  
Georg Kneer ◽  
Jochen Mattay ◽  
Gerhard Raabe ◽  
Carl Krüger ◽  
Jürgen Lauterwein
Keyword(s):  
Malic Acid ◽  
Acid Synthesis ◽  
Alder Reaction ◽  
Diels Alder ◽  
Tert Butyl ◽  
Diels Alder Reaction

scholarly journals An ortho-quinone methide based strategy towards the rubromycin spiroketal family

RSC Advances ◽  
2015 ◽  
Vol 5 (98) ◽  
pp. 80212-80215 ◽  
Author(s):  
N. J. Willis ◽  
C. D. Bray
Keyword(s):  
Diels Alder ◽  
Quinone Methide

A method for the generation/in situhetero-Diels–Alder cycloaddition of a trisubstitutedortho-quinone methide (o-QM) is described.

ChemInform Abstract: A New Synthesis of 1,5-Di-tert-butyl-1,3-cyclopentadiene by Dehydration of an Epoxide and Characterization of Its Diels-Alder Dimer.

ChemInform ◽  
2010 ◽  
Vol 27 (20) ◽  
pp. no-no
Author(s):  
R. P. HUGHES ◽  
A. S. KOWALSKI ◽  
J. R. LOMPREY ◽  
D. R. NEITHAMER
Keyword(s):  
Diels Alder ◽  
Tert Butyl ◽  
New Synthesis
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