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タイトル: Reactions of oxalyl chloride with 1,2-cycloalkanediols in the presence of triethylamine
著者: Itaya, Taisuke
Iida, Takehiko
Natsutani, Itaru
Ohba, Masashi link image
大場, 正志
発行日: 2002年 1月
出版社(者): 日本薬学会
雑誌名: Chemical and Pharmaceutical Bulletin
ISSN: 0009-2363
巻: 50
号: 1
開始ページ: 83
終了ページ: 86
キーワード: 1,2-cycloalkanediol cyclocondensation
Cyclic carbonate ester
Cyclic oxalate ester
Oxalyl chloride
Stereocontrolled cyclization
Stereoelectronic effect
抄録: The relationship between the product patterns and the configurations of 1,2-cycloheptane- and 1,2-cyclooctanediols 9 in the cyclocondensations with oxalyl chloride in the presence of tricthylamine at 0°C has been shown analogous to that obtained for 1,2-disubstituted acyclic ethylene glycols 1: cis-1,2-cyclooctanediol (9f) produced the cyclic oxalate 14f as the major product, while trans-1,2-cycloheptanediol (9e) and trans-1,2-cyclooctanediol (9g) formed the cyclic carbonates 12e, g as the major products. On the other hand, the cyclic oxalates 14a-d were formed as the major products from 1,2-cyclopentane- and 1,2-cyclohexanediols regardless of the configuration. These results can be accounted for by assuming the boat-like transition states for cyclizations of the half esters of comparatively rigid five- and six-membered diols 9a-d. The cyclic oxalates 14a, c may be directly formed through the resulting tetrahedral intermediates from cis-diols (9a, c), and the cyclic carbonates 12a, c as the minor products after ring inversion of the tetrahedral intermediates. The tetrahedral intermediates from the trans-isomers 9b,d cannot undergo ring inversion, producing no traces of the cyclic carbonates 12b,d. © 2002 Pharmaceutical Society of Japan.
DOI: 10.1248/cpb.50.83
URI: http://hdl.handle.net/2297/7560
関連URI: http://www.jstage.jst.go.jp/article/cpb/50/1/50_83/_article/-char/en
資料種別: Journal Article
版表示: publisher
出現コレクション:2.査読済論文(薬)

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