SOLID-STATE PHOTOCYCLODIMERIZATION OF 1-THIOCOUMARIN (=2H-1-BENZOTHIOPYRAN-2-ONE)

被引:13
作者
KLAUS, CP [1 ]
THIEMANN, C [1 ]
KOPF, J [1 ]
MARGARETHA, P [1 ]
机构
[1] UNIV HAMBURG,INST ORGAN CHEM,D-20146 HAMBURG,GERMANY
关键词
D O I
10.1002/hlca.19950780504
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Irradiation (<lambda > 390 nm) of 2H-1-benzothiopyran-2-one (1) in the solid state affords selectively 6a alpha,6b alpha,12b alpha,12c alpha-tetrahydrocyclobuta[1,2-c:4,3-c']bis[1]benzothiopyran-6,7-dione (2), the head-to-head (HH) cis-cisoid-cis dimer, while irradiation of 1 in the solid stare using shorter wavelengths (lambda > 340 nm) affords a mixture of all four cis-fused tricyclic dimers 2-5. These results represent a novel wavelength effect in solid-state photochemistry.
引用
收藏
页码:1079 / 1082
页数:4
相关论文
共 10 条
[1]   TOPOCHEMISTRY .1. SURVEY [J].
COHEN, MD ;
SCHMIDT, GMJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JUN) :1996-+
[2]   A STUDY ON THE PHOTOCHEMICAL DIMERIZATION OF COUMARINS IN THE SOLID-STATE [J].
GNANAGURU, K ;
RAMASUBBU, N ;
VENKATESAN, K ;
RAMAMURTHY, V .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2337-2346
[3]   PHOTOCYCLOADDITIONS TO 1-THIOCOUMARIN [J].
KARBE, C ;
MARGARETHA, P .
JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 57 (1-3) :231-233
[4]   (6A-ALPHA,6B-BETA,12B-BETA,12C-ALPHA)-6A,6B,12B,12C-TETRAHYDROCYCLOBUTA[1,2-C-4,3-C']-DI[1]BENZOTHIOPYRAN-6,7-DIONE [J].
KOPF, J ;
MAELGER, H ;
THIEMANN, C ;
MARGARETHA, P .
ACTA CRYSTALLOGRAPHICA SECTION C-STRUCTURAL CHEMISTRY, 1994, 50 :1922-1924
[5]   PHOTO-C4-CYCLODIMERISATION VON CUMARIN [J].
KRAUCH, CH ;
FARID, S ;
SCHENCK, GO .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (02) :625-&
[6]   SOLID-STATE PHOTODIMERIZATION OF COUMARIN IN THE PRESENCE OF A CRYSTAL LATTICE-CONTROLLING SUBSTANCE [J].
MENG, JB ;
FU, DC ;
YAO, XK ;
WANG, RJ ;
MATSUURA, T .
TETRAHEDRON, 1989, 45 (22) :6979-6986
[7]  
METHCOHN O, 1978, SYNTHESIS-STUTTGART, P56
[8]   PHOTOCHEMICAL-REACTIONS OF ORGANIC-CRYSTALS [J].
RAMAMURTHY, V ;
VENKATESAN, K .
CHEMICAL REVIEWS, 1987, 87 (02) :433-481
[9]  
TAYLOR EC, 1960, TETRAHEDRON LETT, V25, P1
[10]  
Venkatesan K., 1991, PHOTOCHEMISTRY ORG C, P133