183312-23-4

Upstream product

• 32359-01-6 hexenylmagnesium bromide 
• 183312-34-7 2-(3,3-dimethylbut-1-yn-1-yl)benzaldehyde 
• 693-03-8 n-butyl magnesium bromide 
• 917-92-0 3,3-Dimethylbut-1-yne 

Downstream Products

• 183312-07-4 1-(3,3-Dimethyl-but-1-ynyl)-2-[3-(diphenyl-phosphinoyl)-hepta-1,2-dienyl]-benzene 
• 187800-26-6 Acetic acid 1-[2-(3,3-dimethyl-but-1-ynyl)-phenyl]-hept-2-ynyl ester 
• 913256-06-1 C₂₆H₃₀O 

Relevant academic research and scientific papers

Synthesis of Novel Enyne-Allenes, Their Thermal C2-C6 Cyclization, and the Importance of a Benzofulvene Biradical in the DNA Strand Cleavage

Novel enyne-allenes without acceptor substituents have been prepared from propargyl acetates by Pd-catalyzed addition of arylzinc chloride or by cuprate addition. Their thermal reaction afforded exclusively the C2-C6 and no Myers-Saito cyclization products. In one case, intermolecular hydrogen abstraction and DNA strand cleavage were observed.

Steric effects in enyne-allene thermolyses: Switch from the Myers-Saito reaction to the C2-C6-cyclization and DNA strand cleavage

The thermal reaction of enyne-allenes 1 with large substituents (tert.-butyl, trimethylsilyl) at the acetylene terminus leads to C2-C6 cyclization products presumably via an intermediate benzofulvene biradical, whereas with a hydrogen substituent the expected Myers-Saito cycloaromatization product is formed. Effective DNA strand scission can be observed when no intramolecular pathway is available.