Download PDF
Synthesis 1991; 1991(11): 996-998
DOI: 10.1055/s-1991-26627
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
29 April 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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).