Multinuclear NMR structural characterization of an unprecedented photochromic allene intermediate

被引：21

作者：

Delbaere, S

Micheau, JC

Vermeersch, G ^{[1
]}

机构：

[1] Univ Lille 2, UMR CNRS 8009, Fac Pharm, Phys Lab, F-59006 Lille, France

[2] Univ Lille 2, UMR CNRS 8009, Fac Pharm, LARMN, F-59006 Lille, France

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 18期

关键词：

D O I：

10.1021/ol0264859

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An o-allenyl-p-methoxyphenol intermediate (Int) was for the first time proved to be involved in the photochromic reaction of 2,2-di(4-fluorophenyl)-6-methoxy-2H-1-chromene (FC). Transoid-cis (TC) and transoid-trans (TT) photomerocyanines and the intermediate Int are generated by UV irradiation of FC. Visible light converts TC and TT into Int. The monitoring of the reactions was carried out on the basis of H-1, C-13, F-19, and H-2 NMR spectroscopy.

引用

页码：3143 / 3145

页数：3

共 20 条

[1] Femtosecond transient absorption spectroscopy of non-substituted photochromic spirocompounds [J].

Antipin, SA ;

Petrukhin, AN ;

Gostev, FE ;

Marevtsev, VS ;

Titov, AA ;

Barachevsky, VA ;

Strokach, YP ;

Sarkisov, OM .

CHEMICAL PHYSICS LETTERS, 2000, 331 (5-6) :378-386

[2] PHOTOCHROMISM OF SYNTHETIC AND NATURALLY OCCURRING 2H-CHROMENES AND 2H-PYRANS [J].

BECKER, RS ;

MICHL, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (24) :5931-&

[3]

Bertelson R.C., 1971, TECHNIQUES CHEM, VIII, P45

[4] PHOTOCHROMIC PROCESSES IN SPIRO(1,3,3-TRIMETHYLINDOLO-2,2'-NAPHTH[1,2-B]-1,4-OXAZINE) STUDIED USING 2-LASER 2-COLOR TECHNIQUES [J].

BOHNE, C ;

FAN, MG ;

LI, ZJ ;

LUSZTYK, J ;

SCAIANO, JC .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (07) :571-572

[5] LASER PHOTOLYSIS STUDIES OF PHOTOCHROMIC PROCESSES IN SPIROOXAZINES - SOLVENT EFFECTS ON PHOTOMEROCYANINE BEHAVIOR [J].

BOHNE, C ;

FAN, MG ;

LI, ZJ ;

LIANG, YC ;

LUSZTYK, J ;

SCAIANO, JC .

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1992, 66 (01) :79-90

[6] Conical intersection mechanism for photochemical ring opening in benzospiropyran compounds [J].

Celani, P ;

Bernardi, F ;

Olivucci, M ;

Robb, MA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10815-10820

[7] PHOTOCHROMISM OF SPIROINDOLINONAPHTHOXAZINE .1. PHOTOPHYSICAL PROPERTIES [J].

CHU, NYC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1983, 61 (02) :300-305

[8] Kinetic and structural studies of the photochromic process of 3H-naphthopyrans by UV and NMR spectroscopy [J].

Delbaere, S ;

Luccioni-Houze, B ;

Bochu, C ;

Teral, Y ;

Campredon, M ;

Vermeersch, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (05) :1153-1157

[9]

Delbaere S, 2001, PHOTOCHEM PHOTOBIOL, V74, P694, DOI 10.1562/0031-8655(2001)074<0694:NSAKAO>2.0.CO

[10]

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