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Photoisomerization of tetramethylaliene dimer: a facile 1,5-hydrogen shift

✍ Scribed by Edgar F. Kiefer; James Y. Fukunaga

Book ID
104248578
Publisher
Elsevier Science
Year
1969
Tongue
French
Weight
140 KB
Volume
10
Category
Article
ISSN
0040-4039

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✦ Synopsis

Although +,hblTSSl 1,5-shifts Sl'b chbmiaa~ analogs havb babn rbpomd. considbrablb intbrbst in VibW Of thb 1968; received in LK for publication 7 February 1969) wbll known In both cyclic and ocycUc systans, few photo-Thb rbVbPSb iS tX'Ub for 1,7-shifts. ThbSb I'baCtiOns Arb Of altbrnatb stbrbochbmical mdbs postul.ated for SipDIPtrCpiC , rbarrangbmbnts by WOOdWSrd Sti Hoffmann? photochbmical l,5-ati thbmd 1,3-Snd l,'l-mS.FWmgbmbnts should rbquirb antarafacial transfer of thb migrating substitubnt, whloh in mast of thb molboulbs studied to datb could not bb achlbvbd without prohibitivb molbculSr distortion. 2 Hydrogbn atom shifts arb of particular signiflcancb in this connection, since II) antlbordlng c-orbital is aVai.hblb to providb a SynmIbtry-a11OWbd psthway for suprafacial transfbr.2 & authentic cash of an antprafacial l,S-shift has ybt to bb dbscrlbbd. We wish to rbport an bxamplb of a rapid and specific photochbraicbl 1,LhydrCgbn shift in a SyStbm which UniqUbly favors antarSfSCia1 trSnSfbr.

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Kinetic study of a homodienyl-[1,5]-hydr
Kinetic study of a homodienyl-[1,5]-hydrogen shift in a vinylzaziridine
✍ Anita HussΓ©nius; Peter Somfai; David Tanner πŸ“‚ Article πŸ“… 1996 πŸ› John Wiley and Sons 🌐 English βš– 260 KB

The thermal rearrangement of an N-substituted vinylaziridine to the corresponding (Z)-allylic imine, i.e. a homodienyl-[1,5]-hydrogen shift, was studied at different temperatures in the range 40-90 "C. 'H NMR spectroscopy was used to follow the reaction. Rate constants and activation parameters were