Unusual rearrangements of cis-4,7-disubstituted 4,7-dihydro-4,7-dihydroxy[2.2]paracyclophanes on dehydration:: Stereoselective formation of planar chiral cyclohexadienones

被引：10

作者：

Vorontsova, N ^{[1
]}

Rozenberg, V ^{[1
]}

Vorontsov, E ^{[1
]}

Antonov, D ^{[1
]}

Starikova, Z ^{[1
]}

机构：

[1] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 2003卷 / 04期

关键词：

carbonyl compounds; cyclohexadienones; cyclophanes; rearrangement; stereoselectivity;

D O I：

10.1002/ejoc.200390119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under acid conditions, cis-4,7-disubstituted 4,7-dihydro-4,7-dihydroxy[2.2]paracyclophanes undergo dehydration accompanied by rearrangement, affording cyclohexadienone derivatives as major products and with polysubstituted phenols being formed as minor products. The formation of either an ortho or a para semiquinoid system, as well as the configuration of the newly formed asymmetric center, depended strictly on the nature of the substituent (alkyl, allyl, or phenyl). The structures of 3,4-dihydro-3,7-dimethyl[2.2]paracyclophane-4-one (10), 3,7-diallyl-3,4-dihydro[2.2]paracyclophane-4-one (12), and 4,7-dihydro-7,8-diphenyl[2.2]paracyclophane-4-one (22) were determined by X-ray structural analysis. [2.2]Paracyclophane-4,7-quinone (1) was obtained in optically active form.

引用

页码：761 / 770

页数：10

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