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  • 标题:Studies in Stereochemistry. VI. Solvolysis Reactions of dl-cis-2-Benzoylaminocyclohexyl Tosylate
  • 本地全文:下载
  • 作者:Tanezo Taguchi ; Masaharu Kojima
  • 期刊名称:Chemical and Pharmaceutical Bulletin
  • 印刷版ISSN:0009-2363
  • 电子版ISSN:1347-5223
  • 出版年度:1955
  • 卷号:3
  • 期号:5
  • 页码:351-356
  • DOI:10.1248/cpb1953.3.351
  • 出版社:The Pharmaceutical Society of Japan
  • 摘要:dl-cis-2-Benzoylaminocyclohexyl tosylate was submitted to solvolysis in four of the sets of conditions : (a) In absolute ethanol, (b) in 60% ethanol, (c) in water, and (d) in dry acetic acid. The reactions gave rise to cyclohexanone and dl-cis-2-benzoyloxy-cyclohexylamine tosylate commonly in a, b, c, and d, dl-trans-2-benzoyloxycylohexyl-amine tosylate in b and c, and dl-2-ethoxycyclohexylamine tosylate only in a. The reaction mechanisms were discussed. By adaptation of Winstein's and McCasland's procedures the dl-cis-N-benzoyl-O-tosylate was synthesized and showed m.p. 174∼175°, higher than those reported by these authors. Besides, by McCasland's procedure, dl-cis-2-tosylaminocyclohexyl benzozate was formed.
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