SYNTHESIS AND STEREOCHEMICAL BEHAVIOR OF 1-ARYLOCTAHYDROISOBENZOFURO[7A,1-D]OXAZOLE RING-SYSTEM - NEW EXAMPLES OF ISOLABLE ROTAMERS

被引:16
作者
SAITO, K
YAMAMOTO, M
YAMADA, K
机构
[1] Graduate School of Science and Technology, Chiba University, Chiba-shi, 260
关键词
D O I
10.1016/S0040-4020(01)81284-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Preparation and stereochemical behavior of new examples of isolable rotamers are described. Reaction of hydroxylactone 2 with isocyanates 3 - 11 gave the corresponding 12 - 20 in good yields. Among them, ortho di-substituted ones gave isolable rotamers. The behavior of ortho mono-substituted derivatives is also discussed.
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页码:4549 / 4558
页数:10
相关论文
共 13 条
[1]  
Binsch G, 1968, TOP STEREOCHEM, V3, P97
[2]   CARBON-13 MAGNETIC RESONANCE .8. THEORY OF CARBON-13 CHEMICAL SHIFTS APPLIED TO SATURATED HYDROCARBONS [J].
CHENEY, BV ;
GRANT, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1967, 89 (21) :5319-&
[3]  
FRANKELCONRAD H, 1944, J AM CHEM SOC, V66, P845
[4]  
GADIAN DG, 1982, NUCLEAR MAGNETIC RES
[5]  
Levy G.C., 1980, CARBON 13 NUCLEAR MA, P55
[6]   VERY SLOW ROTATION ABOUT A CARBON-CARBON SINGLE BOND IN ORTHO-TOLYL-1,1'-DIADAMANTYLCARBINOL AND RELATED-COMPOUNDS [J].
LOMAS, JS ;
DUBOIS, JE .
TETRAHEDRON, 1981, 37 (12) :2273-2278
[7]  
OKI M, 1983, TOP STEREOCHEM, V14, P1
[8]   UNUSUALLY HIGH BARRIERS TO ROTATION INVOLVING TETRAHEDRAL CARBON-ATOM [J].
OKI, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (02) :87-93
[9]   REACTIVITIES OF STABLE ROTAMERS .30. BROMINE ADDITION TO ROTAMERIC 1-(9-FLUORENYL)-2-(1-METHYLVINYL)NAPHTHALENE - FATE OF INTERMEDIATE CATIONS PRODUCED BY BROMINE CATION ATTACK [J].
OKI, M ;
SHIONOIRI, K ;
OTAKE, K ;
ONO, M ;
TOYOTA, S .
CHEMISTRY LETTERS, 1991, (04) :597-600
[10]  
OKI M, 1990, B CHEM SOC JPN, V63, P3550