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Uncatalyzed, Solvent‐Free [2+2] Cycloaddition of Cyclic Ketene Trimethylsilyl Acetals with Electrophilic Acetylenes
Author(s) -
Miesch Michel,
Wendling Florence
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200010)2000:20<3381::aid-ejoc3381>3.0.co;2-q
Subject(s) - ketene , chemistry , dimethyl acetylenedicarboxylate , trimethylsilyl , electrophile , cycloaddition , furan , medicinal chemistry , ketone , organic chemistry , catalysis
Cyclic ketene trimethylsilyl acetals reacted with electrophilic acetylenes (ethyl propynoate, dimethyl acetylenedicarboxylate and ethynyl methyl ketone) to afford the corresponding [2+2] cycloadducts. The reactions were run at room temperature, without a catalyst and under solvent‐free conditions. α‐Alkylidenelactones, β‐oxocyclobutanecarboxylates and substituted furan derivatives proved to be readily available from the [2+2] cycloadducts by treatment either with TBAF in THF solution or with BF 3 ·Et 2 O.