1,3-DIPOLAR CYCLOADDITION ON HETEROCYCLES .31. CYCLOADDITIONS OF NITRILE OXIDES AND NITRONES TO 4,4-METHYLENE-1-METHYLPIPERIDINE - STUDIES IN REGIOSELECTIVITY AND STEREOSELECTIVITY

Authors
FISERA L SAUTER F FROHLICH J FENG Y ERTL P MEREITER K
Citation
L. Fisera et al., 1,3-DIPOLAR CYCLOADDITION ON HETEROCYCLES .31. CYCLOADDITIONS OF NITRILE OXIDES AND NITRONES TO 4,4-METHYLENE-1-METHYLPIPERIDINE - STUDIES IN REGIOSELECTIVITY AND STEREOSELECTIVITY, Monatshefte fuer Chemie, 125(5), 1994, pp. 553-563
Citations number
26
Categorie Soggetti
Chemistry
Journal title
Monatshefte fuer Chemie → ACNP
ISSN journal
00269247
Volume
125
Issue
5
Year of publication
1994
Pages
553 - 563
Database
ISI
SICI code
0026-9247(1994)125:5<553:1COH.C>2.0.ZU;2-7
Abstract
A series of spiro-substituted isoxazole derivatives were synthesized b y 1,3-dipolar cycloadditions of nitrile oxides and nitrones to 4,4-met hylene-1-methylpiperidine. Since nmr studies confirmed that only one r egioisomer was formed selectively, semi-empirical quantum mechanical m ethods (AM1) were used to rationalize this regiochemical preference vi a calculation and inspection of HOMO-LUMO-energy and coefficients. X-r ay structure analysis carried out for one of these products showed the occurrence of only one stereoisomer, explicable by comparing AM1-calc ulated DELTAH(f)-values of all possible cycloadducts.