ALKOXIDE-INDUCED RING-OPENING OF METHOXYMETHYLIDENE-SUBSTITUTED HOMOPHTHALIC ANHYDRIDE .2. STRUCTURE AND CONFORMATIONAL-ANALYSIS OF THE DIHYDROISOCOUMARIN PRODUCTS

被引：7
作者：
HUTCHINGS, MG [1 ]
CHIPPENDALE, AM [1 ]
SHUKLA, R [1 ]
MCPARTLIN, M [1 ]
机构：
[1] POLYTECH N LONDON,SCH CHEM,LONDON N7 8DB,ENGLAND
来源：
TETRAHEDRON | 1991年 / 47卷 / 37期
关键词：
D O I：
10.1016/S0040-4020(01)81942-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The title reaction leads to a stable acid-ester, an isocoumarin and the two isomeric 3-methoxy-4-methoxycarbonyldihydroisocoumarins. X-ray structure determination of one of these isomers reveals a trans-diaxial conformation. N.m.r. data indicate this geometry also pertains in solution. H-1-C-13 vicinal coupling constants for the alternative cis-isomer correspond to equatorial-3-methoxy, axial-4-methoxycarbonyl. The trends of two C-13 n.m.r. chemical shifts are opposite to those suggested by literature precedents. Empirical force field calculations are consistent with the experimentally determined conformations.
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页码：7869 / 7874
页数：6
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