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Unusual rearrangement upon dehydration ofcis-4,7-diallyl-4,7-dihydroxy-4,7-dihydro[2.2]paracyclophane

✍ Scribed by N. V. Vorontsova; V. I. Rozenberg; E. V. Vorontsov; D. Yu. Antonov; Yu. N. Bubnov

Publisher
Springer
Year
2000
Tongue
English
Weight
94 KB
Volume
49
Category
Article
ISSN
1573-9171

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## Abstract 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 eit

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Cycloaddition of PTAD to 7-methylenenorbornene (1 a) afforded the rearrangement urazole 2a, but not with 7-(pheny1methylene)norbornene (1 b) and 7-(chloromethylene)norbornene (lc). Instead, besides the [2 + 23 cycloadducts 3b and 3c, respectively, l b gave the double [4 + 23 adduct 4b and l c the no