Stereoselectivities of Diels-Alder cycloadditions of tricyclic dienes to MTAD, PTAD, and N-methylmaleimide

被引:8
作者
Marchand, AP
Dong, EZ
Shukla, R
Prasad, AD
Bott, SG
机构
[1] Department of Chemistry, University of North Texas, Denton
关键词
D O I
10.1016/S0040-4020(97)10002-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Diels-Alder cycloadditions of 1,2,3,4,9,9-hexachloro-1 alpha,4 alpha,4a alpha,8a beta-tetrahydro-1,4-methanonaphthalene (5) and 1,2,3,4,9,9-hexachloro-1 alpha,4 alpha,6,7-tetrahydro-1,4-methanonaphthalene (6) to 4-methyl- and 4-phenyl-1,2,4-triazoline-3,5-di-one [MTAD and PTAD, respectively] and to N-methylmaleimide (NMM) have been studied. The structures of several of the resulting cycloadducts were determined unequivocally by X-ray crystallographic methods. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:14895 / 14902
页数:8
相关论文
共 19 条
[1]   Synthesis and base promoted intramolecular nucleophilic reaction of 8-hydroxy-1,2,3,4-tetrachloro-9,9-dimethoxy-1 alpha,4 alpha,4a alpha,6,7,8 beta,8a alpha-hexahydro-1,4-methanonaphthalene-5(1H)-one [J].
Bott, SG ;
Marchand, AP ;
Bolin, JC ;
Wang, YJ ;
Prasad, AD ;
Xing, DX ;
Talafuse, LK ;
Watson, WH ;
Bourne, SA ;
Carlson, TF .
JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1995, 25 (10) :641-651
[2]   SIR88 - A DIRECT-METHODS PROGRAM FOR THE AUTOMATIC SOLUTION OF CRYSTAL-STRUCTURES [J].
BURLA, MC ;
CAMALLI, M ;
CASCARANO, G ;
GIACOVAZZO, C ;
POLIDORI, G ;
SPAGNA, R ;
VITERBO, D .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1989, 22 :389-393
[3]   DIELS-ALDER ADDITIONS OF HEXACHLOROCYCLOPENTADIENE TO SOME 7-SUBSTITUTED NORBORNADIENES [J].
BYRNE, LT ;
RYE, AR ;
WEGE, D .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (09) :1961-1969
[4]   SYNTHESIS AND REACTIONS OF 1,4,4A,5,8,8A-HEXAHYDRO-1,4-METHANO-5,8-ETHENONAPHTHALENE [J].
CHOW, TJ ;
CHAO, YS .
SYNTHETIC COMMUNICATIONS, 1988, 18 (15) :1875-1881
[5]   DIASTEREOFACIAL SELECTIVITY IN DIELS-ALDER CYCLOADDITIONS OF METHYL ACRYLATE TO FACIALLY DIFFERENTIATED UNSYMMETRICAL CYCLOHEXA-1,3-DIENES [J].
COXON, JM ;
FONG, ST ;
LUNDIE, K ;
MCDONALD, DQ ;
STEEL, PJ ;
MARCHAND, AP ;
ZARAGOZA, F ;
ZOPE, UR ;
RAJAGOPAL, D ;
BOTT, SG ;
WATSON, WH ;
KASHYAP, RP .
TETRAHEDRON, 1994, 50 (45) :13037-13048
[6]   FACIAL DIFFERENTIATION IN DIELS-ALDER REACTIONS TO DISSYMMETRIC CYCLOHEXA-1,3-DIENES [J].
COXON, JM ;
MACLAGAN, RGAR ;
MCDONALD, DQ ;
STEEL, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (07) :2542-2549
[7]   PI-FACIAL SELECTIVITY IN DIELS-ALDER REACTIONS OF HEXACYCLO[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]PENTADECA-5,7-DIENE-3,10-DIONE [J].
COXON, JM ;
OCONNELL, MJ ;
STEEL, PJ .
JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (21) :4726-4732
[8]  
COXON JM, 1994, ADV DET R M, V3, P131
[9]  
Cromer D. T., 1974, INT TABLES XRAY CRYS, V4
[10]   SIGMA-PI INTERACTION AS A CONTROLLING FACTOR IN THE STEREOSELECTIVITY OF ADDITION-REACTIONS [J].
GLEITER, R ;
PAQUETTE, LA .
ACCOUNTS OF CHEMICAL RESEARCH, 1983, 16 (09) :328-334