Rearrangement of cyclic allenes via 1,2-dehydro[10]annulenes: Intramolecular dehydro Diels-Alder of 3-(trimethylsilyl)propiolamides

Synthesis

Volumn , Issue 5, 2004, Pages 761-764

  Rodríguez, David ^a   Castedo, Luis ^a   Domínguez, Domingo ^a   Saá, Carlos ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Alkynes; Allenes; Amides; Annulenes; Diels Alder reactions

Indexed keywords

MOLECULAR DYNAMICS; ORGANIC COMPOUNDS; POLYAMIDES; REACTION KINETICS; SOLVENTS;

CYCLIC ALLENES; INTRAMOLECULAR DEHYDRO DIELS-ALDER REACTIONS;

SYNTHESIS (CHEMICAL);

ALLENE DERIVATIVE; AMIDE; ANNULENE DERIVATIVE;

ARTICLE; DIELS ALDER REACTION; MOLECULAR DYNAMICS; REACTION ANALYSIS; SYNTHESIS;

EID: 1942424982     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815984     Document Type: Article

References (15)

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11. For synthesis of unsubstituted propiolamides, see: Coppola, G. M.; Damon, R. E. Synth. Commun. 1993, 23, 2003.
12. Compounds 6a-c were also rather unstable, decomposing rapidly under acidic conditions. In fact, under the Pd-catalyzed coupling conditions both 5 and 6 decomposed slowly, making it necessary to optimize the reaction time. Long reaction times did not afford the desired products.
13. 4
14. Minor amounts of the benzo[f]isoindol-1-one 2b (10%) and its desilylated derivative (not shown, 9%) were also observed in this case.
15. 2) should be 5E,7Z.