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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

このアイテムを引用あるいはリンクする場合は次の識別子を使用してください。 http://hdl.handle.net/2297/7560



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