SINGLE STEP FORMATION OF NOVEL TRICYCLIC SYSTEMS ON [3+2] PHOTOCYCLOADDITION OF 3-(1-ALKYNYL)CYCLOHEXENONES TO METHOXYALKENES

被引:7
作者
MARGARETHA, P [1 ]
RATHJEN, HJ [1 ]
AGOSTA, WC [1 ]
机构
[1] ROCKEFELLER UNIV LABS,NEW YORK,NY 10021
关键词
D O I
10.1016/S0040-4039(00)89034-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Irradiation of 1b (λ n ̃350 nm) in tert-butyl alcohol solution containing 5 leads to the novel ring system 9b in a single step. Similar reactions occur between 1a and both 5 and 6. Mechanisms of these transformations are discussed. © 1990.
引用
收藏
页码:3245 / 3248
页数:4
相关论文
共 10 条
[1]   PHOTOCHEMISTRY OF 4,4-DIMETHYL-1-MESITYL-2-PENTYN-1-ONE [J].
AGOSTA, WC ;
CALDWELL, RA ;
JAY, J ;
JOHNSTON, LJ ;
VENEPALLI, BR ;
SCAIANO, JC ;
SINGH, M ;
WOLFF, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (10) :3050-3057
[2]  
HUSSAIN S, 1981, TETRAHEDRON S PRINT, V37, P3305
[3]   NOVEL (3 + 2) PHOTOCYCLOADDITIONS WITH 3-(1-ALKYNYL)CYCLOHEXENONES AND TETRAMETHYLETHYLENE [J].
MARGARETHA, P ;
RATHJEN, HJ ;
WOLFF, S ;
AGOSTA, WC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (13) :841-842
[4]   LIGHT-INDUCED REACTIONS OF 1,1,1-TRIFLUORO-3-DECYN-2-ONE WITH OLEFINS [J].
MARGARETHA, P ;
SCHRODER, C ;
WOLFF, S ;
AGOSTA, WC .
JOURNAL OF FLUORINE CHEMISTRY, 1986, 30 (04) :429-437
[5]   KETENE ACETALS .23. DEALCOHOLATION OF ORTHOESTERS WITH ALUMINUM TERT-BUTOXIDE [J].
MCELVAIN, SM ;
DAVIE, WR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (04) :1400-1402
[6]   SOME [2 + 2] AND [3 + 2] PHOTOCYCLOADDITIONS OF ALPHA,BETA-ACETYLENIC KETONES [J].
RAO, VB ;
SCHRODER, C ;
MARGARETHA, P ;
WOLFF, S ;
AGOSTA, WC .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20) :3881-3884
[7]   NOVEL CYCLIZATION OF TYPE-II BIRADICALS FROM ALPHA-BETA-ACETYLENIC KETONES [J].
RAO, VB ;
WOLFF, S ;
AGOSTA, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (02) :521-522
[8]   PHOTODECARBONYLATION OF 2,5,5-TRIMETHYL-2-(1-PROPYNYL)CYCLOPENTANONE - 1,5-RING VS 1,4-RING CLOSURE OF A PROPARGYL-ALKYL BIRADICAL [J].
RUDOLPH, A ;
MARGARETHA, P ;
AGOSTA, WC .
HELVETICA CHIMICA ACTA, 1987, 70 (02) :339-341
[9]   ALPHA-PHENYLSELENYLATION OF ZIRCONIUM OR ALUMINUM ENOLATES [J].
SCHWARTZ, J ;
HAYASI, Y .
TETRAHEDRON LETTERS, 1980, 21 (16) :1497-1500
[10]   PHOTOCHEMICAL [3 + 2] CYCLOADDITION REACTIONS OF ALKYNONES - DIVERSE FATES OF 2 SIMILAR VINYLCARBENE INTERMEDIATES AND REACTIONS OF A CYCLOPROPENOL [J].
WOLFF, S ;
AGOSTA, WC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (08) :2363-2367