Control factors of two reaction modes of pentacoordinate 1,2-oxasiletanides, the Peterson reaction and memo-brook rearrangement

被引：21

作者：

Naganuma, K

Kawashima, T

Okazaki, R

机构：

[1] Univ Tokyo, Grad Sch Sci, Dept Chem, Bunkyo Ku, Tokyo 1130033, Japan

[2] Japan Womens Univ, Fac Sci, Dept Chem & Biol Sci, Bunkyo Ku, Tokyo 1128681, Japan

来源：

CHEMISTRY LETTERS | 1999年 / 11期

关键词：

D O I：

10.1246/cl.1999.1139

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Thermolyses of pentacoordinate 1,2-oxasiletanides with or without a neopentyl group at the 3-position in the presence of a proton source afforded the corresponding olefin and/or alcohol, indicating that they are the intermediates of both the Peterson reaction and home-Brook rearrangement which are two possible modes in the reaction of beta-hydroxyalkylsilanes with bases.

引用

收藏

页码：1139 / 1140

页数：2

相关论文

共 15 条

[1]

Ager D. J., 1990, ORG REACTIONS, V38, P1, DOI DOI 10.1002/0471264180.0R038.01

[2]

AGER DJ, 1984, SYNTHESIS-STUTTGART, P384

[3] PROTIODESILYLATION REACTIONS OF SIMPLE BETA-HYDROXYSILANES (AND ALPHA-HYDROXYSILANES) - HOMO-BROOK REARRANGEMENTS [J].

HUDRLIK, PF ;

HUDRLIK, AM ;

KULKARNI, AK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (24) :6809-6811

[4]

Kawashima T, 1996, SYNLETT, P600

[5] Generation and decomposition of a pentacoordinate spirobis[1,2-oxasiletanide] [J].

Kawashima, T ;

Naganuma, K ;

Okazaki, R .

ORGANOMETALLICS, 1998, 17 (03) :367-372

[6] SYNTHESIS AND X-RAY CRYSTALLOGRAPHIC ANALYSIS OF PENTACOORDINATE 1,2-OXASILETANIDES, INTERMEDIATES OF THE PETERSON REACTION [J].

KAWASHIMA, T ;

IWAMA, N ;

OKAZAKI, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (19) :7598-7599

[7] DIRECTED DILITHIATION OF HEXAFLUOROCUMYL ALCOHOL - FORMATION OF A REAGENT FOR THE FACILE INTRODUCTION OF A STABILIZING BIDENTATE LIGAND IN COMPOUNDS OF HYPERVALENT SULFUR (10-S-4), PHOSPHORUS (10-P-5), SILICON (10-SI-5), AND IODINE (10-I-3) [J].

PEROZZI, EF ;

MICHALAK, RS ;

FIGULY, GD ;

STEVENSON, WH ;

DESS, DB ;

ROSS, MR ;

MARTIN, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (06) :1049-1053

[8] BASE-CATALYZED REARRANGEMENT OF BETA-HYDROXYVINYLSILANES TO ALLYL SILYL ETHERS [J].

SATO, F ;

TANAKA, Y ;

SATO, M .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (04) :165-166

[9] PREPARATION OF ALKYL SILYL ACETALS FROM CARBOXYLIC ESTERS WITH TERT-BUTYLDIMETHYLSILYLDIHALOMETHYLLITHIUM - 1,3-REARRANGEMENT OF SILYL GROUP FROM CARBON TO OXYGEN [J].

SHINOKUBO, H ;

OSHIMA, K ;

UTIMOTO, K .

CHEMISTRY LETTERS, 1995, (06) :461-462

[10] tert-butyldimethylsilyldihalomethyllithium as a dihalomethylene dianion synthon. 1,3-rearrangement and 1,4-rearrangement of silyl group from carbon to oxide [J].

Shinokubo, H ;

Miura, K ;

Oshima, K ;

Utimoto, K .

TETRAHEDRON, 1996, 52 (02) :503-514