106536-23-6

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 513-42-8 3-hydroxy-2-methyl-1-propene 
• 847661-06-7 2-methylprop-2-ene-1-sulfonyl fluoride 
• 97142-86-4 1-(4-chlorophenyl)but-2-yn-1-ol 
• 1383536-73-9 1-chloro-4-(3-methylbuta-1,2-dien-1-yl)benzene 

Downstream Products

• 14276-94-9 (3-methylbutyl)-4-chlorobenzene 

Relevant academic research and scientific papers

Gold-catalyzed isomerization of unactivated allenes into 1,3-dienes under ambient conditions

We have developed a gold-catalyzed isomerization of unactivated allenes into 1,3-dienes with nitrosobenzene as an additive. This reaction proceeded almost exclusively at room temperature for highly substituted allenes. The utility of this reaction is manifested by the development of one-pot [4+2]-cycloaddition of allenes and reactive alkenes.

One-pot synthesis of 1-aryl-3-methyl-1,3-dienes using methallyl(trimethyl) silane and aldehydes and their low temperature (Z)→(E) isomerization induced by sulfur dioxide

2-Methylprop-2-ene-1-sulfonyl fluorides can be easily prepared via the ene reaction of methallylsilanes and SO2. In the presence of a base, aldehydes and 2-methylprop-2-ene-1-sulfonyl fluorides give 1,3-(E) and (Z)-dienes. Their (Z)→(E) isomerization by classical means fails or leads to their polymerization. It is shown that SO2 can isomerize 1-aryl-3-methyl-1,3-dienes at low temperature, without formation of sulfolenes (cheletropic addition/elimination). Preliminary mechanistic studies suggest that SO2 adds to 1,3-dienes forming 1,4-diradical intermediates that are responsible for the (Z)→(E) isomerizations.

THE ONE-POT PALLADIUM CATALYZED WITTIG REACTION WITH ALLYLIC ALCOHOLS. SCOPE AND LIMITATIONS

Some allylic alcohols react with aldehydes and triphenylphosphine in a one-pot formal Wittig reaction under Pd0 catalysis.The method has been extended to cinnamyl alcohol, 1, 2-methyl-2-propen-1-ol, 7, and 3-buten-2-ol, 11, and to heterocyclic aldehydes.