Science of Synthesis

Kubik, S., Science of Synthesis, (2010) 41, 531.

Alkenediazonium compounds are strongly electrophilic at the 2-position (see Section ‌41.7.2‌). Reaction with nucleophiles that add to this position therefore furnishes new alkenediazonium derivatives if a leaving group can be cleaved from the substrate. This reaction presumably follows an addition–elimination mechanism via intermediate diazo compounds.

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‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeeeeee Meeeeeeeeeeeeee Meeeeeeee[‌888‌]

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8-Meeeeee-8,8-eeeeeeeeeee-8-eee-8-eeeeeeeee Meeeeeeeeeeeeeeeeeee (‌88‌):[‌888‌]

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8-Meeeee-8-(eeeeeeeeee)eeeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeee (‌88‌):[‌888‌]

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(8,8-Meeeeeeeeeeeeeeeeeee-8-eeeeeee)eeeeeeeeeeeeeeee Meeeeeeeeeeeeeeeeeee (‌88‌):[‌888‌]

M eeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeee eeeeeeeeeeeeeeeeeeee (‌88‌; 8.88 e, 88.8 eeee) ee MM8Me8 (88 eM) eee eeeee eeeeeeee ee e eeee ee M,M′-eeeeeeeeeeeeee-8,8-eeeeeee (8.88 e, 88.8 eeee) ee MM8Me8 (88 eM) eeee eee eeeeeee ee −88°M. Meeeeeee eee eeeeeeeee ee −88°M eee 88 eee. Meeeeeeeee, eee eeeeeee eee eeeeeee ee eeee ee ee ee, eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeee eeee MeMM (88 eM) eee 88 eee. Mee eeeee eeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeeeeee ee MM8Me8, eee eeeeeeeeeeee eeeee ee eeeeeeee ee MMe8 (MMMMMMM: eeeee); eeeee: 8.88 e (88%); ee 888°M (eee).

Mee eeeeeeeeeeeee MMe8− eeee eee eeeeeeee ee eeeeeeee eee eeeeeeeeee eeeeeeee eeee e eeee ee MMMe8 (8.8 e, 88.8 eeee) ee MeMM (88 eM) ee 8°M, eeeeeeee eee 88 eee, eee eeeeeeeeee. Me eee eeeeeeee ee eeeeeeeeee ee MeMM eee eeeeeeee eeeeeeeeeeeee ee eeeeeeee ee MMM; eeeee: 8.88 e (88%); ee 888°M (eee).

8,8-Meeeeeeeeeeeeeeeeeeeeeeeeee Meeeeeeeeeeeeeeee (‌88‌):[‌888‌]

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References