Addition of p-toluenesulphonyl azide to photochemically generated 2-azabicyclo[4.2.0]oct-3-enes 1 and 2 produced toluene-4-sulphonylimines 3 and 4, whereas the same intermediates 1 and 2 with dimethyl acetylenedicarboxylate gave 2-azabicyclo[6.2.0]deca-3,5-diene, 5, and 2-azatricyclo[6.2.0.0(3,6]dec-4-enes 6 and 7. The cyclobutene ring of 6 and 7 was selectively opened under mild conditions to afford the dienes 8 and 9, respectively.
Donati, D., Fusi, S., Ponticelli, F. (1994). Addition reactions on 2-azabicyclo[4.2.0]oct-3-enes. GAZZETTA CHIMICA ITALIANA, 124(3), 121-124.
Addition reactions on 2-azabicyclo[4.2.0]oct-3-enes
DONATI, D.;FUSI, S.;PONTICELLI, F.
1994-01-01
Abstract
Addition of p-toluenesulphonyl azide to photochemically generated 2-azabicyclo[4.2.0]oct-3-enes 1 and 2 produced toluene-4-sulphonylimines 3 and 4, whereas the same intermediates 1 and 2 with dimethyl acetylenedicarboxylate gave 2-azabicyclo[6.2.0]deca-3,5-diene, 5, and 2-azatricyclo[6.2.0.0(3,6]dec-4-enes 6 and 7. The cyclobutene ring of 6 and 7 was selectively opened under mild conditions to afford the dienes 8 and 9, respectively.
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https://hdl.handle.net/11365/6713
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