REARRANGEMENT OF 3-METHYL-2-(4-SUBSTITUTED PHENYL)-1,3-OXAZOLINIUM 3-METHYLIDES

被引：26

作者：

KITANO, T ^{[1
]}

SHIRAI, N ^{[1
]}

SATO, Y ^{[1
]}

机构：

[1] NAGOYA CITY UNIV, FAC PHARMACEUT SCI, TANABE DORI, MIZUHO KU, NAGOYA, AICHI 467, JAPAN

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1992年 / 40卷 / 03期

关键词：

NITROGEN YLIDE; SOMMELET-HAUSER REARRANGEMENT; STEVENS REARRANGEMENT; RING ENLARGEMENT; CYCLIC AMINE; ORGANOSILICON COMPOUND; AMMONIUM SALT; FLUORIDE ION;

D O I：

10.1248/cpb.40.768

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

2-(4-Substituted phenyl)oxazolidinium 3-methylides (5), prepared by fluoride ion-induced desilylation of 3-methyl-2-(4-substituted phenyl)-3-(trimethylsilyl)methyl-1,3-oxazolinium iodides (4), rearranged to 4-methyl-2-(4-substituted phenyl)morpholines (8, Stevens rearrangement products) as the main products.

引用

页码：768 / 769

页数：2

共 14 条

[1]

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[2]

KITANO T, 1991, SYNTHESIS-STUTTGART, P996

[3]

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[4]

MACHIDA Y, 1991, SYNTHESIS-STUTTGART, P117

[5]

MARCH J, 1985, ADV ORG CHEM, P992

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[8]

Pine S. H., 1970, ORG REACTIONS, V18, P403

[9] YLIDE REARRANGEMENT OF BENZYLTRIALKYLAMMONIUM SALTS - THE IMPROVED SOMMELET-HAUSER REARRANGEMENT .2. [J].

SHIRAI, N ;

SATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (01) :194-196

[10] INTERMEDIATE IN SOMMELET-HAUSER REARRANGEMENT OF N,N-DIMETHYLBENZYLAMMONIUM N-METHYLIDES [J].

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SATO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2767-2770

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