135522-27-9

Upstream product

• 90-02-8 salicylaldehyde 
• 164513-96-6 1,1-dimethyl-2-propenyl isobutyl carbonate 
• 1111-97-3 3-chloro-3-methylbut-1-yne 
• 135522-22-4 2-(1',1'-dimethylpropargyloxy)benzaldehyde 

Downstream Products

• 135522-28-0 2-(1',1'-dimethylallyloxy)benzaldoxime 
• 151731-50-9 2,2-dimethyl-8-(3-methyl-2-butenyl)-2H-chromene-6-carboxylic acid 

Relevant academic research and scientific papers

Cascade Claisen and Meinwald Rearrangement for One-Pot Divergent Synthesis of Benzofurans and 2 H-Chromenes

A new cascade approach has been developed for the one-pot four-step divergent synthesis of polysubstituted benzofurans and 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/Meinwald rearrangement/dehydrative or oxidative cyclization. This new method was demonstrated with 39 examples tolerating different substitutions at an epoxide, allylic ether, and aromatic ring, and we showcased its utility with the first total synthesis of natural product liparacid A in seven steps.

A cascade Claisen rearrangement/o-quinone methide formation/electrocyclization approach to 2H-chromenes

A new approach has been developed for the synthesis of 8-substituted 2H-chromenes, featuring a novel cascade aromatic Claisen rearrangement/o-quinone methide formation/6π-electrocyclization. This new method was demonstrated with 28 examples tolerating different substitutions at alkenes, allylic and aromatic ring and with total syntheses of three 2H-chromene natural products.

X=Y-ZH systems as potential 1,3-dipoles. Part 31. Generation of nitrones from oximes, background and scope of the tandem 1,2-prototropy-intramolecular cycloaddition sequence

1,2-Prototropy in aryl and aliphatic oximes generates a small equilibrium concentration of the corresponding NH nitrone. Examples of a tandem 1,2-prototropy-intramolecular cycloaddition sequence involving aryl and aliphatic oximes are described and steric and electronic factors that favour or disfavour such a sequence are discussed. Deuterium labelling studies with an aliphatic oxime rule out the involvement of an enehydroxylamine in the prototropic generation of the NH nitrone.