192128-11-3

Upstream product

• 73084-25-0 (4-trimethylsilyl-1,3-butadiynyl)lithium 
• 341970-20-5 2-[4-(2-methoxymethylphenyl)buta-1,3-diyn-1-yl]benzaldehyde 
• 4526-07-2 1,4-bis(trimethylsilyl)-1,3-butadiyne 
• 1046118-23-3 1-methoxymethyl-2-(buta-1,3-diynyl)benzene 
• 266674-51-5 1-methoxymethyl-2-[4-(trimethylsilyl)buta-1,3-diynyl]benzene 
• 18982-54-2 o-bromobenzyl alcohol 
• 90003-91-1 1-iodo-2-(methoxymethyl)benzene 
• 52711-30-5 1-bromo-2-(methoxymethyl)benzene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 341970-39-6 2-[4-(2-methoxymethylphenyl)buta-1,3-diyn-1-yl]benzyl alcohol 

Relevant academic research and scientific papers

Effect of water molecules on the cycloaromatization of non-conjugated aromatic tetraynes

Cycloaromatization of the thienyl tetrayne 1, which was prepared in several steps from bis(trimethylsilyl)butadiyne and 3-bromothiophene-2-carbaldehyde, in benzene (0.33 mM) in the presence of molecular sieves 3A at room temperature gave the indeno[2,1-b]thiophene ring-fused 1H-2-benzopyran derivative 10 and indeno[2,1-b]thiophene derivative 11 in 11 and 40% yields, respectively. In contrast, cycloaromatization of 1 in the presence of water molecules at room temperature gave the indeno[2,1-b]thiophene ring-fused 1H-2-benzopyran derivative 10 and the indene ring-fused indeno[2,1-b]thiophene derivative 12 in 82 and 14% yields, respectively. Cycloaromatization of the phenyl tetrayne 9 in the presence of water molecules at room temperature also resulted in a dramatic change in product yields.

Synthesis of indeno[1,2-b]phenanthrene-type heterocycles by cycloaromatization of acyclic non-conjugated benzotetraynes

A novel and simple procedure for the preparation of 6-oxa-, 6-thia-, and 6-azaindeno[1,2-b]phenanthrenes (4) by thermal cycloaromatization of acyclic non-conjugated benzotetraynes (3) is described.

Cycloaromatization of a non-conjugated polyenyne system: Synthesis of 5H-benzo[d]fluoreno[3,2-b]pyrans via diradicals generated from 1-[2-{4-(2-alkoxymethylphenyl)butan-1,3-dinyl}]phenylpentan-2,4-diyn -1-ols and trapping evidence for the 1,2-didehydrobenzene diradical

Non-conjugated tetraynes 1 undergo thermal intramolecular cyclization to non-benzenoid diradicals (23) followed by radical cycloaromatization at 25°C to provide 7-dehydro-5H-benzo[d]fluoreno[3,2-b]pyran monoradical (24) and alkyl radicals (25). Hydrogen abstraction of 24 gives 5H-benzo[d]fluoreno[3,2-b]pyrans (3) which are converted to 4 by reaction with 25. On the other hand, 2 gives 5H-fluorenol (5), indicating the formation of 1,2-didehydrobenzene diradical intermediates (28 and 29). These radicals are trapped as the corresponding Diels-Alder-type products by reaction with an aromatic diene, anthracene.