Tetrahedron letters

Transformation of tetrahydropyranyl ether of allylic alcohol into 7-octene-1, 5-diol by means of trialkylmanganate

T Nishikawa, T Nakamura, H Kakiya, H Yorimitsu…

Index: Nishikawa, Toshihiro; Nakamura, Tomoaki; Kakiya, Hirotada; Yorimitsu, Hideki; Shinokubo, Hiroshi; Oshima, Koichiro Tetrahedron Letters, 1999 , vol. 40, # 36 p. 6613 - 6616

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Citation Number: 5

Abstract

Triethylmanganate (Et 3 MnMgBr) was also effective as tributylmanganate. However, trimethylmanganate derived from MnCl 2 and MeMgI was not effective for the transformation. For instance, treatment of 1f with Me 3 MnMgI gave a methylated product (1,4-pentanediol) in only 13% in addition to unidentified complex products. The use of n-Bu 3 MnLi derived from n-BuLi instead of n-BuMgBr afforded 2a in only 31% yield along with 3a (7%). ... Hexadecane could be detected in ...