PHOTOCHEMICAL-REACTIONS OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH STABILIZED YLIDES TO PRODUCE PUSH-PULL CAPTODATIVE ALLENES

被引：29

作者：

SESTRICK, MR ^{[1
]}

MILLER, M ^{[1
]}

HEGEDUS, LS ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1992年 / 114卷 / 11期

关键词：

D O I：

10.1021/ja00037a008

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Photolysis of chromium alkoxycarbene complexes in the presence of stabilized ylides produced allenes having electron withdrawing groups on C-1 and electron donating groups on C-3. These highly reactive captodative allenes rearranged to 1,3-substituted-1,3-dienes under mildly acidic conditions and hydrolyzed to gamma-keto-alpha,beta-unsaturated esters, both in excellent yield.

引用

收藏

页码：4079 / 4088

页数：10

相关论文

共 63 条

[41] SYNTHESIS AND CHARACTERIZATION OF STABLE N-PHTHALIMIDYL-2,3-BUTADIENOATES [J].

KATHAWALA, FG ;

SCHUSTER, HF ;

SHAPIRO, MJ .

TETRAHEDRON LETTERS, 1981, 22 (38) :3703-3706

[42] SELECTIVE REDUCTIONS .22. FACILE REDUCTION OF ALPHA, BETA-UNSATURATED ALDEHYDES AND KETONES WITH 9-BORABICYCLO[3.3.1]NONANE - REMARKABLY CONVENIENT PROCEDURE FOR SELECTIVE CONVERSION OF CONJUGATED ALDEHYDES AND KETONES TO CORRESPONDING ALLYLIC ALCOHOLS IN PRESENCE OF OTHER FUNCTIONAL-GROUPS [J].

KRISHNAMURTHY, S ;

BROWN, HC .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (07) :1197-1201

[43] SIMPLE SYNTHESIS OF ALKYL ALLENECARBOXYLATES (ALLENIC ESTERS) BY THE WITTIG-REACTION [J].

LANG, RW ;

HANSEN, HJ .

HELVETICA CHIMICA ACTA, 1980, 63 (02) :438-455

[44]

LEROUX Y, 1973, TETRAHEDRON LETT, P2585

[45]

MANTIONE R, 1969, B SOC CHIM FR, P4523

[46] A PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF ALPHA,ALPHA-DIARYL-2-PYRROLIDINEMETHANOL - PREPARATION AND CHEMISTRY OF THE CORRESPONDING OXAZABOROLIDINES [J].

MATHRE, DJ ;

JONES, TK ;

XAVIER, LC ;

BLACKLOCK, TJ ;

REAMER, RA ;

MOHAN, JJ ;

JONES, ETT ;

HOOGSTEEN, K ;

BAUM, MW ;

GRABOWSKI, EJJ .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :751-762

[47] PYRIDINIUM PARA-TOLUENESULFONATE - MILD AND EFFICIENT CATALYST FOR TETRAHYDROPYRANYLATION OF ALCOHOLS [J].

MIYASHITA, M ;

YOSHIKOSHI, A ;

GRIECO, PA .

JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (23) :3772-3774

[48]

OHRUI H, 1978, TETRAHEDRON LETT, P2095

[49] DERIVATIVES OF FLUORENE [J].

PINCK, LA ;

HILBERT, GE .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (03) :723-723

[50]

POUGNY JR, 1978, TETRAHEDRON LETT, P3301

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