NOVEL PHOTOCHEMICAL-REACTION OF 2-(2-ALKYNYL)ACETOPHENONES INITIATED BY TYPE-II ABSTRACTION

被引：5

作者：

KRAVITZ, JI ^{[1
]}

MARGARETHA, P ^{[1
]}

AGOSTA, WC ^{[1
]}

机构：

[1] ROCKEFELLER UNIV LABS,NEW YORK,NY 10021

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 01期

关键词：

D O I：

10.1016/S0040-4039(00)71210-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of 5a and 5b in methanol leads to formation of the diastereomeric methoxy alcohols 8a and 9a, and 8b and 9b, respectively. These reactions can be understood as involving type II abstraction of gamma-hydrogen, 1,5 cyclization of the resulting biradical 6 to form vinyl carbene 7 (as 1 --> 2), and then carbene insertion into the hydroxyl group of solvent methanol.

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页码：31 / 34

页数：4

相关论文

共 18 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]

ALLINGER NL, 1981, QUANT CHEM PROGRAM E, V13, P395

[3]

ALLINGER NL, 1976, QCPE, V11, P318

[4]

[Anonymous], 1981, SYNTHESIS ACETYLENES

[5]

BELLAMY LJ, 1976, INFRARED SPECTRA COM, pCH6

[6]

HUET F, 1978, SYNTHESIS-STUTTGART, P63

[7]

HUSSAIN S, 1981, TETRAHEDRON S PRINT, V37, P3305

[8] 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

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

MARGARETHA, P ;

RATHJEN, HJ ;

AGOSTA, WC .

TETRAHEDRON LETTERS, 1990, 31 (23) :3245-3248

[10] 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