Spirocyclic Meisenheimer complexes: XLII. Intramolecular alkylation of O-picryl amino alcohols with a tertiary amino group

Authors
Knyazev, VN Borbulevich, OY Shishkin, OV
Citation
Vn. Knyazev et al., Spirocyclic Meisenheimer complexes: XLII. Intramolecular alkylation of O-picryl amino alcohols with a tertiary amino group, RUSS J ORG, 36(5), 2000, pp. 706-711
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
10704280 → ACNP
Volume
36
Issue
5
Year of publication
2000
Pages
706 - 711
Database
ISI
SICI code
1070-4280(200005)36:5<706:SMCXIA>2.0.ZU;2-C
Abstract
Dimethyl(2-picryloxyethyl)- and dimethyl(3-picryloxypropyl)amines do not fo rm zwitterionic spirocyclic 2,4,6-trinitrocyclohexadienide (Meisenheimer) a dducts but undergo intramolecular alkylation to give, respectively, tetrame thylpiperazinium and dimethylazetidinium picrates. Likewise, spirocyclic tr initrocyclohexadienide complex with a 4-morpholiniomethyl-1,3-dioxolane rin g is regioselectively converted into 2-hydroxy-7-oxa-4-azoniaspiro[3.5]nona ne picrate whose structure was proved by X-ray analysis.