High Pressure-Promoted [2+2] Cycloaddition Reactions of 4-Methylphenyl 1,2-Propadienyl Sulfone with Enol Ethers

Under high pressure conditions, 4‐methylphenyl 1,2‐propadienyl sulfone (1) and enol ethers (6) undergo regioselective [2+2] cycloaddition reactions to give (3‐alkoxycyclobutylidene)methyl 4‐methylphenyl sulfones (7). The cycloaddition reaction has a broad scope with respect to the substituents allow...

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Bibliographic Details
Published in:European journal of organic chemistry 2003-03, Vol.2003 (5), p.894-897
Main Authors: Aben, René W. M., Braverman, Samuel, Scheeren, Hans W.
Format: Article
Language:English
Subjects:
1-Alkoxybuta-1
1‐Alkoxybuta‐1,3‐dienes
3-Alkoxymethylene cyclobutanes
3-dienes
Allenes
Cycloadditions
High-pressure chemistry
Regioselectivity
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Summary:Under high pressure conditions, 4‐methylphenyl 1,2‐propadienyl sulfone (1) and enol ethers (6) undergo regioselective [2+2] cycloaddition reactions to give (3‐alkoxycyclobutylidene)methyl 4‐methylphenyl sulfones (7). The cycloaddition reaction has a broad scope with respect to the substituents allowed at the enol ether. The synthetic potential of the obtained cycloadducts is illustrated by a stereoselective addition of dimethylamine to the double bond of 7a and 7b to yield 11a and 11b and by a tertiary amine‐induced double bond isomerisation of 7a and 7b, followed by ring‐opening of the cyclobutene intermediate to yield 1‐alkoxybuta‐1,3‐dienes 12a and 12b. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200390135