RING-OPENING OF AZETIDINOLS BY PHENOLS - REGIOCHEMISTRY AND STEREOCHEMISTRY

被引：25

作者：

HIGGINS, RH ^{[1
]}

FAIRCLOTH, WJ ^{[1
]}

BAUGHMAN, RG ^{[1
]}

EATON, QL ^{[1
]}

机构：

[1] NE MISSOURI STATE UNIV,DIV SCI,KIRKSVILLE,MO 63501

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 08期

关键词：

D O I：

10.1021/jo00087a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Ring opening of a series of 1-alkyl- and 1-benzyl-3-azetidinols by 6-bromophenol without added base is reported. Opening of trans-2-methyl- and cis- and trans-2-phenyl-3-azetidinols is highly regioselective, if not regiospecific. The 2-methyl compounds open by cleavage of the N-C4 bond and the 2-phenyl compounds by cleavage of the N-C2 bond in a highly stereoselective, if not stereospecific, manner, which involves inversion of configuration at C2. The results are rationalized in terms of nucleophilic ring opening of the azetidinium ions.

引用

页码：2172 / 2178

页数：7

共 24 条

[1] AZETIDINES .3. TOSYLATION AND ACYLATION OF 1-SUBSTITUTED 3-AZETIDINOLS . PREPARATION OF 1-T-BUTYLAZETIDINE-3-CARBOXYLIC ACID
CHEN, TY
SANJIKI, T
KATO, H
OHTA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1967, 40 (10) : 2401 - +
[2] PARAMAGNETIC INDUCED SHIFTS IN PROTON MAGNETIC RESONANCE SPECTRA OF ALCOHOLS USING TRIS(DIPIVALOMETHANATO)EUROPIUM(III)
DEMARCO, PV
ELZEY, TK
LEWIS, RB
WENKERT, E
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (19) : 5734 - +
[3] NUCLEAR MAGNETIC RESONANCE SPECTRA OF SOME 1-ALKYL-2-PHENYL-3-AROYLAZETIDINES AND RELATED COMPOUNDS . DISPERSION EFFECTS AND CONFORMATIONAL ANALYSIS
DOOMES, E
CROMWELL, NH
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (02) : 310 - &
[4] THE LITHIUM ALUMINUM HYDRIDE REDUCTION OF PARA-SUBSTITUTED STILBENE OXIDES
FELDSTEIN, A
VANDERWERF, CA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (06) : 1626 - 1631
[5] FREHEL D, 1977, EUR J MED CHEM, V12, P447
[6] DIRECTION OF RING OPENING IN THE REDUCTION OF PARA-SUBSTITUTED STYRENE OXIDES WITH LITHIUM BOROHYDRIDE
FUCHS, R
VANDERWERF, CA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (06) : 1631 - 1634
[7] CYCLIZATION OF 1-ALKYLAMINO-3-HALO-2-ALKANOLS ATO 1-ALKYL-3-AZETIDINOLS
GAERTNER, VR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1967, 32 (10) : 2972 - &
[8] RING-OPENING NUCLEOPHILIC ALKYLATIONS BY TERTIARY AZETIDINESS
GAERTNER, VR
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1969, 6 (03) : 273 - &
[9] CONFIGURATION AND CONFORMATION ISOMERISM OF AZETIDINES
HIGGINS, RH
DOOMES, E
CROMWELL, NH
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1971, 8 (06) : 1063 - &
[10] STEREOCHEMISTRY, KINETICS, AND MECHANISM OF HYDROLYSIS OF 3-AZETIDINYL TOSYLATES
HIGGINS, RH
CROMWELL, NH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (01) : 120 - 124

← 1 2 3 →