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An addition—cyclization—elimination mechanism for dehydro Diels-Alder reactions

✍ Scribed by Bernard Miller; Dumitru Ionescu

Publisher: Elsevier Science
Year: 1994
Tongue: French
Weight: 252 KB
Volume: 35
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)73449-6

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✦ Synopsis

Vmylacetylene 1 undergoes reactions with dienopNles by a mechanism involving initial addition of acids to the triple bond, cycloaddition, and elimination of add. For more than half a century the fact that vinylacetylenes can undergo cycloaddition reaclions with dienophiles ("dehydro Die&Alder reactions"11 has puzzled organic chemists. ti the mechantom~ of the cycloadditions are similar to those of Diels-Alder reactions the initial products would he 1,2-cyclohexadi or I~J-cydohexatrienea -highly atmined interxmxliates which are unlikely to he formed unQr the mild conditions reported tar 901~ dehydro Dick+Alder reactions. Fu&ermore, to yield the observed products these internv&ates would~~taundagol~~~ehifts,,althollgh~shifteorenotcommontyotwervedincydicsllenea2

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