137744-76-4

Upstream product

• 67-56-1 methanol 
• 107-93-7 (E)-but-2-enoic acid 
• 36942-56-0 3-bromo-4-methylanisole 
• 95152-22-0 (2E)-N-(4-methoxyphenyl)-2-butenamide 
• 20007-99-2 Wieland-Miescher ketone 

Relevant academic research and scientific papers

Iodine-methanol induced novel fragmentation of bicyclic diones to anisole derivatives

The cyclic diones (1), (5), (8) and (11) on treatment with iodine and methanol underwent fragmentation yielding the anisole derivatives (4), (6), (9) and (12) respectively.

Reaction of 2-Butenoic Acid Dianion and Its N-(4-Methoxyphenyl)amide with Methoxy-Substituted Arynes

N-(4-Methoxyphenyl)-1-butenamide dianion (6), generated by the reaction of N-(4-methoxyphenyl)-2-butenamide (3) with LDA or LTMP, undergoes exclusive 4-arylation with various methoxy-substituted arynes 2a-e yielding mixtures consisting of a N-(4-methoxyphenyl)-(E)-4-aryl-3-butenamide (9) (85-90percent) and a N-(4-methoxyphenyl)-(E)-4-aryl-2-butenamide 9' (10-15percent).Under certain conditions, 4,4-diarylated products 12 are also obtained. 2-Butenoic acid dianion (14) also reacts with methoxy-substituted arynes affording predominantly 4-aryl-3-butenoic acids 15 and minor amountsof 4-aryl-2-butenoic acids 15'.The exclusive low temperature (-30 to -40 deg C) 4-addition of arynes to dianion 14 is in contrast to the predominant 2-addition that 14 undergoes with certain aldehydes and ketones at comparable temperatures.The mixtures of 4-arylbutenoic acids 15 and 15' and 4-arylbutenamides 9 and 9' were readily hydrogenated (Pd/C) and esterified (MeOH/H2SO4) to synthetically valuable methyl 4-arylbutanoates 17.