Dienophilic thioaldehydes

E Vedejs, TH Eberlein, DL Varie

Index: Vedejs, E.; Eberlein, T. H.; Varie, D. L. Journal of the American Chemical Society, 1982 , vol. 104, # 5 p. 1445 - 1447

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Citation Number: 98

Abstract

In earlier work, we had found that transient S= CHCN (from Br2CHCN+ EtOCS; K+) could be trapped by 2-ethoxybutadiene to give the Diels-Alder adduct in 15% yield. Ic A report that a thioaldehyde generated by Norrish Cleavage of a phenacyl sulfide C6H5COCH2SCH2Y, 1 (Y= a penicillin-derived fragment) can be trapped in more respectable yield (55% thiirane using a diphenyldiazomethane trap) 4 encouraged us to reexamine the Diels-Alder ...