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Nucleophilic aromatic substitution - a route to the naphthaline system from α-cyclopropylstyrene

✍ Scribed by S. Brenner; E. Dunkelblum

Publisher: Elsevier Science
Year: 1973
Tongue: French
Weight: 217 KB
Volume: 14
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)96186-6

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✦ Synopsis

Alkyllitkum reagents add to O(-cyclopropylstyrene (I) to produce cyclopropylcarb~nyllithium derivatives wkch undergo ring-operung to the corresponding styrenes 14

These additions were achieved either by using isopropyllitluum in 1) ether or with BULI-mDA (tetramethylethylenediamine) complex in hexane2). We have shown that the intermedlate carbaxnon II ring-opens rapidly to produce the isomeric ~18 and m anions III and IV, 111 an approximate ratio of l:l, wkch could be trapped by protonation

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