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Studies on the antitumor agent CC-1065 : 1-Phenylsulfonyl-1,3-butadiene. An electrophilic equivalent to 1,3-butadiene for the synthesis of 3,31-bipyrroles.

✍ Scribed by Serge Halazy; Philip Magnus

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
184 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Sequential conjugate additions of methyl, TOSMIC anion and TOSMIC anion to I-pkenyZsuZfonyZ-1,3-butadiene provides a direct route to 3,3l-bipyrroles, andillustrates that I-pkenylsuZfonyZ-1,3-butadiene can functionas an electropkilic 1,3-butadiene equivalent.

Recently we reported the synthesis of the rare 3,3l-bipyrrole

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Transition states for the Diels-Alder reactions of 2,3-diaza-1,3-butadiene with ethylene, formaldehyde, formaldimine, cis-and frans-diazene, and nitrosyl hydride were located by ab initio molecular orbital calculations. The bond orders of the new forming bonds have been used to determine the asynchr