Science of Synthesis

Salaün, J., Science of Synthesis, (2005) 26, 568.

Keteniminium salts, readily available from α-chloro enamines and a Lewis acid,[‌55‌] are highly electrophilic molecules. They undergo [2+2] cycloaddition with nonactivated and even electrophilic alkenes, giving cyclobutaniminium salts, which provide cyclobutanones when hydrolyzed.[‌56‌] They have therefore been used as ketene equivalents in cycloadditions with alkenes; moreover, they have the advantage of not dimerizing.

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‌Meeeee 88‌ Meeeeeeeee Meeeeeeee ee e Meeeeeee Meeeeeeeeeeee ee Meeeeeeeeeeee ee e Meeeee Meeeeeeeeeee Meee ee Meeeeeeeeeee[‌88‌]

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‌Meeeee 88‌ Meeeeeeeeee ee e Meeeeeee Meeeeeeeeeeee ee Meeeeeeeeeeeee Meeeeeeeeeeee ee e Meeeeeeeeeee Meee eeee e Meeeee Meee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeeeeeee[8.8.8]eeeeee-8-eee (‌88‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee eeeee ‌88‌ (888 ee, 8.8 eeee) [eeeeeeee ee 88% eeeee eeee 8-eeeeeeeeee-8-eeeee eeee (8 eeeee), eeeeee eeeeeeee (8 eeeee), eee Me8MM (8 eeeee)] ee eee eeeeeee (8 eM) (MMMMMMM: eeeeeeeeee) eeeee M8 eee eeeee 8,8,8-eeeeeeeeeeeeeeeee (88 ee, 8.88 eeee, 8.88 eeeee), eee eee eeee eee eeeeeeee. M eeee ee Me8M (888 ee, 8.88 eeee, 8.8 eeeee) ee eee eeeeeee (8.8 eM) eee eeeee eeeeee 88 eee ee eeeeeee. Me eeeeee ee eeeeeeee eee eeeeeeeee eeeeee eee eeeeeeeee. Mee eeeeeee eee eeeeeeee eee 8 e, eeeeee ee 88°M, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeeee eee eee eeeeee eeee Me8M eee eeee eeeee ee ee MM8Me8 (8 eM) eee M8M (8 eM). Mee eee-eeeee eeeeeee eee eeeeeee eee 88 e ee ee eee MM8Me8 eee eeeeeee eeeee eeeeeee eeeeeeee ee 88°M ee eeeee e eeeeee eeeeeee eeeee eeeee eee eeeeeeeee eeee MMe8 (8 × 8 eM) (MMMMMMM: eeeee). Mee eeeeeeee MMe8 eeeeeeee eeee eeeeee eeee M8M eee eeeee eee eee eeeeeeee eeeeeee eeeeee eeee eeeeeeeee eeee MM8Me8 (8 × 8 eM). Mee eeeeeeee MM8Me8 eeeeeeee eeee eeeeee eeee M8M eee eeeee. Mee eee eeeeeeeee eeee eeeeeeee eee eeeeee eeeeeee e eeeeee (eeeeee eee); eeeee: 88 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 8888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.