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Synthesis 1991; 1991(11): 996-998
DOI: 10.1055/s-1991-26627
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Rearrangement of 3-Aryl-4-methylmorpholinium-4-methylides

Tomoko Kitano* , Naohiro Shirai, Yoshiro Sato
  • *Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467, Japan
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Publikationsdatum:
29. April 2002 (online)

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Fluoride-ion induced desilylation reaction of 3-Aryl-4-methyl-4-[(trimethylsilyl)methyl]morpholinium iodides 5a,b gave 4-methyl-6-phenyl-1,4-oxazepane (9a, Stevens rearrangement product) from 5a, and 10-methoxy-2-methyl-1,2,3,4,6, 11a-hexahydro-5,2-benzoxazonine (7b) from 5b. In the presence of 1, 8-diazabicyclo[5.4.0]undec-7-ene, however, both reactions afforded 10-substituted 2-methyl-1,2,3, 4,6,7-hexahydro-5,2-benzoxazonines 8a,b (Sommelet-Hauser rearrangement products).