PREPARATION OF ALPHA-SUBSTITUTED S-PHENYLTHIO ESTERS FROM 2-NITRO-2-PHENYLTHIO OXIRANES

被引：17

作者：

ASHWELL, M ^{[1
]}

JACKSON, RFW ^{[1
]}

KIRK, JM ^{[1
]}

机构：

[1] UNIV NEWCASTLE UPON TYNE,DEPT CHEM,BEDSON BLDG,NEWCASTLE TYNE NE1 7RU,TYNE & WEAR,ENGLAND

来源：

TETRAHEDRON | 1990年 / 46卷 / 21期

关键词：

D O I：

10.1016/S0040-4020(01)89058-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Nitro-2-phenylthio oxiranes (3), prepared by nucleophilic epoxidation of 1-nitro-1-phenylthio alkenes (1), react with a variety of heteroatomic nucleophiles to give α-substituted S-phenylthio esters (2). Of special note is the efficient reaction of 2-nitro-2-phenylthio oxiranes with boron trifluoride etherate in toluene at room temperature to give α-fluoro S-phenylthio esters (8). © 1990.

引用

页码：7429 / 7442

页数：14

共 48 条

[1] PREPARATION AND SYNTHETIC UTILITY OF 1-PHENYLTHIO-1-NITRO EPOXIDES - FACILE PREPARATION OF ALPHA-SUBSTITUTED S-PHENYL THIO ESTERS
ASHWELL, M
JACKSON, RFW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (04) : 282 - 283
[2] USEFUL NEW ACYL ANION EQUIVALENTS USING OXIRANYL PHENYL SULFONES
ASHWELL, M
JACKSON, RFW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (04): : 835 - 836
[3] PHENYLSULFONYL OXIRANE - A VERSATILE REAGENT FOR ORGANIC-SYNTHESIS
ASHWELL, M
JACKSON, RFW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (10) : 645 - 647
[4] ASHWELL MA, 1988, SYNTHESIS-STUTTGART, P229
[5] REACTIONS OF NITRO SUGARS .38. REDUCTIVE DENITRATION OF CARBOHYDRATE ALPHA-NITROEPOXIDES BY SODIUM-BOROHYDRIDE
BAER, HH
MADUMELU, CB
[J]. CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1978, 56 (09): : 1177 - 1182
[6] REACTIONS OF NITRO SUGARS .20. ALKALINE EPOXIDATION OF CARBOHYDRATE NITROOLEFINS
BAER, HH
RANK, W
[J]. CANADIAN JOURNAL OF CHEMISTRY, 1971, 49 (19): : 3192 - &
[7] VERY HIGH DIASTEREOFACIAL SELECTIVITY IN THE NUCLEOPHILIC EPOXIDATION OF N-(PARA-TOLYLSULPHONYL)VINYLSULPHOXIMINES
BAILEY, PL
CLEGG, W
JACKSON, RFW
METHCOHN, O
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (01): : 200 - 202
[8] PREPARATION OF ALPHA-SUBSTITUTED S-PHENYL THIO ESTERS FROM ALDEHYDES AND (PHENYLTHIO)NITROMETHANE
BARRETT, AGM
GRABOSKI, GG
RUSSELL, MA
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) : 1012 - 1015
[9] STEREOSELECTIVE SYNTHESES OF S-PHENYL TETRAHYDROFURAN-2-THIOCARBOXYLATE AND TETRAHYDROPYRAN-2-THIOCARBOXYLATE DERIVATIVES USING (PHENYLTHIO)NITROMETHANE
BARRETT, AGM
FLYGARE, JA
SPILLING, CD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (19) : 4723 - 4726
[10] BETA-LACTAM ANNULATION USING (PHENYLTHIO)NITROMETHANE
BARRETT, AGM
GRABOSKI, GG
SABAT, M
TAYLOR, SJ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) : 4693 - 4702

← 1 2 3 4 5 →