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Evidence for a zwitterionic intermediate in the 2+2 cycloaddition of tetracyanoethylene to a trans-fixed 1,3-diene

โœ Scribed by Roll Huisgen; Joaquin Plumet Ortega


Book ID
104246139
Publisher
Elsevier Science
Year
1978
Tongue
French
Weight
193 KB
Volume
19
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


Tetracyanoethylene (TCNE) belongs to the most active dienophiles in . the Diels-Alder reaction.' Trans-fixed 1,3-dienes, however, combine with TCNE in 2+2 cycloadditions to give vinylcyclobutanes; 293 the second double bond effects an activation, No. 41 ACKNOWLEDGMENT. J.P.O. expresses his gratitude to the Alexander von Humboldt-Stiftung for a stipend.


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Evidence for a diradical intermediate in
โœ G. Huybrechts; B. Van Mele ๐Ÿ“‚ Article ๐Ÿ“… 1978 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 254 KB

Despite an extensive literature, controversy about the Diels-Alder reaction mechanism still exists. For the thermal dimerization of 1,3-butadiene, for example, a concerted one-step [I] or two-stage [2] mechanism, a mixture of orbital symmetry allowed and forbidden cycloadditions 131, as well as a tw