16548-22-4

Upstream product

• 18350-44-2 4,4-diethoxy-but-2-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 14444-77-0 diethyl phenyl orthoformate 

Downstream Products

• 5799-77-9 1.1-Diethoxy-4-dimethylaminobutin-(2) 
• 5799-78-0 4-diethylamino-but-2-ynal diethyl acetal 
• 841235-37-8 (2-(4,4-diethoxybut-2-ynyloxy)phenyl)methanol 
• 1027171-50-1 toluene-4-sulfonic acid 2-(4,4-diethoxy-but-2-ynyloxy)-benzyl ester 
• 841235-38-9 1-(4,4-diethoxybut-2-ynyloxy)-2-(iodomethyl)benzene 
• 16548-23-5 4-p-Toluolsulfonyloxybutin-⁽²⁾-al-2.4-dinitro-phenylhydrazon 

Relevant academic research and scientific papers

Solvent and substituent effects on conjugated eliminations in propargylic systems

The deprotonation of 4-methoxy-but-2-ynal diethyl acetal by n- butyllithium induces an acetylenic-allenic isomerization (in diethylether) or a conjugated elimination reaction (in THF), providing the corresponding 1,4- dialkoxycumulene. An allenyllithium, that has been trapped as an allenylstannane, is proposed to be a common intermediate to both pathways. Also, the deprotonation of 4-dialkylamino-but-2-ynal diethyl acetals in the same conditions affords a mixture of (E) and (Z) aminocrotonates of which formation can be explained by a chemioselective removal of the acetalic proton leading to an intermediate allenyllithium that has equally been trapped by stannylation. (C) 2000 Elsevier Science Ltd.

New approaches to bicylic vinyl heterocycles from propargylic acetals

(Chemical Equation Presented) The paper describes further studies on the intramolecular carbolithiation of propargylic acetals with aryllithiums leading to 2-vinylbenzofurans and 3-vinylfuropyridines. Attempts to extend the cascade to [4.4.0] binuclear he