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Title: Synthesis of alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes and their reactivity toward methyllithium.
Authors: Sedenkova, K.; Averina, E.; Borisov, I.; Grishin, Yu.; Rybakov, V.; Kuznetsova, T.; Zefirov, N.
Abstract: A number of new alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes bearing different halogen atoms were synthesized. 1,1-Dihalo-4- tert-butoxyspiro[2.2]pentanes reacted with methyllithium at −55 to −10°C to give exclusively 1- tert-butoxy-2-vinylidenecyclopropane. The reaction of 1-bromo-1-fluoro-4-phenylsulfanylspiro[2,2]pentane with methyllithium resulted in replacement of the fluorine atom by methyl group.
Subjects: ALKOXY compounds; PENTANE; METHYLLITHIUM; HALOGEN compounds; BUTOXY compounds; FLUORINE compounds synthesis; SPECTRUM analysis
Publication: Russian Journal of Organic Chemistry, 2012, Vol 48, Issue 10, p1265
ISSN: 1070-4280
Publication type: Academic Journal
DOI: 10.1134/S1070428012100016

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Synthesis of alkoxy- and phenylsulfanyl-substituted 1,1-dihalospiro[2.2]pentanes and their reactivity toward methyllithium.