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Synthesis 1991; 1991(12): 1209-1215
DOI: 10.1055/s-1991-28421
DOI: 10.1055/s-1991-28421
paper
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The Organocopper Route from (2-Propynylidene)morpholinium Triflates to Morpholinoallenes, 1-Morpholino-1,3-butadienes, and 2-Morpholino-1,3-butadienes
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Publication History
Publication Date:
29 April 2002 (online)
Organocopper reagents undergo conjugate addition to (1,3-diphenyl- and (1-methyl-3-phenyl-2-propynylidene)morpholinium triflates 1a and 1b. The resulting morpholinoallenes can be isolated if the allenic unit bears no CH substituent. Allenes bearing a R1R2 CH substituent at C-3 can be isolated in some cases; their thermal isomerization yields 4-(1,3-diphenyl-1,3-alkadienyl)morpholines 9. Allenes resulting from salt 1b spontaneously isomerize to 2-morpholino-1,3-butadienes 12. Reaction of allylcopper with 1a yields 4-[(3Z and 3E)-1, 3-diphenyl-1,3,5-hexatrienyl]morpholine (8).