50998-59-9

Upstream product

• 719-22-2 2,6-Di-tert-butyl-1,4-benzoquinone 
• 4392-24-9 Cinnamyl bromide 
• 51040-73-4 3,5-di-t-butyl-N-(E)-cinnamyl-4-hydroxy-N,N-dimethylanilinium bromide 
• 10437-44-2 N,N-dimethyl-2,6-ditertiarybutyl-4-amino phenol 
• 50998-57-7 2,6-di-t-butyl-2-(E)-cinnamyl-4-dimethylaminocyclohexa-3,5-dienone 

Relevant academic research and scientific papers

Direct allylation of quinones with allylboronates

Allylboronates undergo C-H allylation of unsubstituted or monosubstituted benzoquinone and naphthoquinone substrates. In the case of 2,5-or 2,6-disubstituted quinones addition involving the substituted carbon takes place. Allylation with stereodefined allylboronates occurs with retention of the configuration.

Base Catalysed Rearrangements involving Ylide Intermediates. Part 14. Rearrangements of 4-Oxidoanilinium Ylides and 3-Oxidoanilinium Betaines

The N-allyl-4-oxidoanilinium ylides (11a-c) undergo a sigmatropic rearrangement at 0 deg C to give initially the products (9a-c), which undergo a further rearrangement to give the isolated reaction products (8a-c).The N-(3,3-dimethylallyl)-4-oxidoanilinium ylide (11d) reacts at 0 deg C by the alternative pathway involving homolysis and radical pair recombination to give a mixture of the products (8d) and (13d).The ylides (15a-c) rearrange by a similar radical pair mechanism.The N-pentadienyl-4-oxidoanilinium ylides derived from the salts (24a and b) also rearrange at 0 deg C by a sequence of and sigmatropic rearrangements to give in each case the product (26b).The N-allyl-3-oxidoanilinium betaines (29a and b) undergo rearrangements on heating at 40 deg C to give mixtures of the products (32) and (33) whereas the N-pentadienyl-3-oxidoanilinium ylide (30) gives only the product (35) of a rearrangement followed by aromatisation.