ORBITAL SYMMETRY CONTROL IN THE NITRONE-OXAZIRIDINE SYSTEM.NITRONE PHOTOSTATIONARY STATES Page: 3 of 7
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I, R' = (CH )2:," =4 CH<
0 hv
III, R' = N0 , R" = CA
A -
IV, R' = O ~" = CH2CH
The nmr spectra of those nitrones at -60* indicated the pr sncc of
only one nitrone isomer, the tran configuration as discussed by Kcyano
and Suzuki. Irradiation of transIA and IA at -60* in CDCD and CDC!;
yielded exclusively trans-oxaziridines,9 as observed by nmr at -S04.
However, under the same conditions in CD3GD, trans-IIIA and VA yelce
a mixture of 69% cis: 31% trans oxaziridines, which was in contrast zc
the predominantly trans-oxaziridines found by Boyd, et al nit succes-
sive partial irradiations of trans-IVA at -60, the presence of cs-: VA
was demonstrated by nmr, and a photostationary state of 37% cis: -w.
trans-IVA was reached at approximately 15% conversion to oxaziridarE-.
The cos-IVA rapidly isomerized thermally to trans-IVA at room tem:ra: re
Tre thermal stability of cis-IiIA and IVA was found to be concen ra fv-
de;endent. They were relatively stable when formed by irradiatioc at
room pemperature in alcoholic solvents in 10- A" (t1/2 ,24 hours). -ne
UV spectrum of the photostationary mixture of IVA was similar 1o onaz
ob gained by dilution of the concentrated solution irradiated in ;he n-r
;uie to the photostationary state at -601. The uv spectrum of c" -:''
was determined from the photoequilibrium ccmpositi-on and the isosbsa:c
poi;* for cis " trans thermal isomzrization.
The ratio of cis and ir ns-IVA at the photostationary stave is m.2:
z arent from the ratio of cis ana ::ans-V3 formed at t e of :
Op.oocyclization reaction. 7cr this reason the quantum y'.e. on
o:oreactions for each isomer were determined at 23* (10- > ard ar
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Splitter, Janet S.; Su, Tah-mun; Ono, Howard & Calvin, Melvin. ORBITAL SYMMETRY CONTROL IN THE NITRONE-OXAZIRIDINE SYSTEM.NITRONE PHOTOSTATIONARY STATES, article, June 1, 1971; Berkeley, California. (https://digital.library.unt.edu/ark:/67531/metadc893302/m1/3/: accessed July 16, 2024), University of North Texas Libraries, UNT Digital Library, https://digital.library.unt.edu; crediting UNT Libraries Government Documents Department.