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23.17.1.1.3.3 Method 3: [2,3]-Sigmatropic Rearrangement of 1-Cyanoalkyl Methylenesulfur Ylides

DOI: 10.1055/sos-SD-023-00727

Perst, H.Science of Synthesis, (200623852.

The simultaneous formation of the ketenimine C=C and C=N bonds by rearrangement of an appropriate precursor is essentially limited to [2,3]-sigmatropic reactions of 1-cyanoalkyl methylenesulfur ylides.[‌290‌‌293‌] Thermal conversions of alkynamines into keten­imines are of minor importance; for an example of this type of process,[‌270‌] see Section 23.17.1.1.3.1.2.

Meeeeee eeeee eeeeeee,[‌888‌,‌888‌] ee eeeeeeeee ee eeee eeeeeeeeee ee 8-eeeeeeeeee eeeeee­eeeeeeeee eeeeee, e.e. 888, eee eeee eeeeeeee eeeee eee eeeeeeee ee eeeeee eeeee 888 ee eeeeee 8-eeeeeeeeeeeeeee 888 eeee M,M-eeeeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee (888) (Meeeee 88).[‌888‌] Mee eeeeeee ee eeeeee eeeeeeeee ee eeeeeeee ee eeeeeeee eeeeeee eeee M-eeeeeeeeeeeeeeeee.[‌888‌] Mee eeeeeeeee ee eee eeeeeeee 888 eeee eee eeeee 888 eee 888 ee eeeeeeeee ee eeeeeee eee e eeeeeeeee eeeeeeeeeeeee eee eeee 888 eee eeeeeeeeee eeeeee eeeeeeee, eeeeeeee eeeeeeeeeee eee eee eeeee 888; eee eeeeee ee eeeeeeeee eee e [8,8]-eeeeeeeeeee eeeeeeeeeeeee eeee eee M-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeee 888.[‌888‌] Mee eeeeeeeee eeee ee ee eeeeeeeee ee eee eeeeeeeeeee (88 ee 8°M), eee eeeeeeeeee eeeeeee eeeee e eeee eeee (88888e). Me eeeeee eeeeeeeeeee, eeeeeeeeeeeee ee eee eeeeeeeee eeeeee eeeeeeeeeeeeeeeeeeee eeee 888 eeeeee eee eeeeeee eeee eeeeeeeee eeeeeee eeee eee eeeeeeeee ee eee eeeeeeeeeee 888.[‌888‌]

Meeeee 88 Me Meee Meeeeeeeee eee [8,8]-Meeeeeeeeee Meeeeeeeeeeee ee 8-Meeeeeeeee Meeeeeeeeeeeeee Meeeee[‌888‌]

M [8,8]-eeeeeeeeeee eeeeeeeeeeeee eee eeee eeee eeeeeee ee eee eeee eeeeeeeee ee 8-eeeee-8,8-eeeeeeee-8,8-eeeeeee-8M-eeeeeeeeeeeeee-8-eee eeeeeeeeeeeeeeeee (888), eeeeeeeee eee eeeeee eeeeeeeeee eeeeeeeeee 888 ee e 8,8-eeeeeeeeeeeeeee eeeeee eee e eeeeee eeeee eeeeeeeeeeee 888 (Meeeee 88).[‌888‌] Mee eeeeee ee eeeeeeeee ee eeee ee eeeeeeeeeeeee ee eee eeeeeeeee eeee 888, eeeee ee eeee ee eeeeeeeeeeee eeeeeeeeee ee M-eeeeeeeeeee ee eee eeeeeeeeeee 8-eeeeee-8,8-eeeeeee-8M-8-eeeeeeeeeeeeee-8-eeeeeeeeeeee (888).[‌888‌]

Meeeee 88 Meeeeeeee ee e 8,8-Meeeeeeee-8,8-eeeeeeeeeeeeeee Meeeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

M-(Meeeeeeeeeeeeee)-M-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

M,M-Meeeeeeeeeeeeeeeeeeeeeeeeeee Meeeeeee (888):[‌888‌]

M eeee ee MMM (88eeee) ee eee MM8Me8 (88eM) eee eeeeee (88°M), eee e eeee ee MMM (88eeee) ee eee MM8Me8 (88eM) eee eeeee. Mee eeee 888 eeeeeeeeeeee, eee eee eeeeeee eee eeeeeee ee eeeee ee 88°M eee 88e eeeeee eee ee eee eeee eeee.

M-(Meeeeeeeeeeeeee)-M-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeee 888:[‌888‌]

Me MeM (88eeee), eeeee eee eeee eeeee eee MMM (88eM), eee eeeee e eeee ee eee eeeeee eeeeeeeeeeeeeeee eeeeeeeeee 888 (88eeee) ee eee MMM (88eM). Meee eee M8 eeeeeeeee eee eeeeee, eee eeeeee ee eeeeeee eeee eee eeeeeeee; eee eeeeeeee eee eeeeee (88 ee 8°M) eee eee eeee eeeee ee eee eeeee-eeeeeeee eeeeeeeeee ee eee eeeeeeeeeeeeeeeeeeee eeeeeeee 888. Meeeeeeeeee ee eee eeeeeeeee eeeee eee eeeeeeee, eeeeeeee ee eeee eeeeeeeeee ee e eeeeeeeeeee (MeMe). Meeee eeeeeeee eee eeeeeeeee eeeeeeee eeeee (M8=MMe8MM 88e; M8=MMeMeMM 888e) ee eee eeeeeeeeeee, eee eeeeeee eee eeeeeeee eee eee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Me eee eeeeeee eeee eeeee M8M (888eM) eee 8M ee MMe (88eM), eee eee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee 8.8M ee MeMM eee eeeee (Me8MM8). Meeee eeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeee eee eeeeeeeeeeeeee [eeeeeee (MMMMMMM: eeeeeeeeee)/eeeeeeeeeee ee Me8M/eeeeeeeeeee] ee eeeee eee eeeeeeeeeee, eeeee eee eeeeeeeeee eeeeeeee ee eeee; eeeee: 8888%.

8-Meeeee-8,8-eeeeeeeee-8,8,8,8-eeeeeeeeee-8,8-eeeeeeeeeeeeeee (888):[‌888‌]

8-Meeee-8,8-eeeeeeee-8,8-eeeeeee-8M-eeeeeeeeeeeeee-8-eee Meeeeeeeeeeeeeeee (888):[‌888‌]

MMMMMMM: Meeeeeeeee, eeeeeeeee, ee eeee eeeeeeeeee ee eeeeeeeeeee eee ee eeeee.

M eeeeeee ee 8-eeeeee-8,8-eeeeeee-8M-8-eeeeeeeeeeeeee-8-eeeeeeeeeeee (888; 8.8e, 8.8eeee), MeM (8.8e, 88eeee), eee MeMM8 (8.8e, 8.8eeee) ee eee MM8Me8 (88eM) eee eeeeeeee eee 88e eeee eeeeeeeee eeee eee eeeee. Mee eeeeeeeeeee eee eeeeeeee eee eee eeeeee eeee eee MeMM. Mee eeeeeeee eeee eeeeeeeeeeee ee eeeeeee ee eeee eeeeeeeee eeeeee; eeeee: 8.8e (88%); ee 888888°M (eeeeeee).

8-Meeeee-8,8-eeeeeeeee-8,8,8,8-eeeeeeeeee-8,8-eeeeeeeeeeeeeee (888):

Me e eeeeeeeeee ee eee eeeee eeeeeeeee eeee 888 (888ee, 8.8eeee) ee eee MMM (88eM) eee eeeee e 88% eeeeeeeeee ee MeM ee eeeeeee eee (888ee, 8.8eeee) eeeee e M8 eeeeeeeeee ee 8°M. Mee eeeeeee eee eeeeeee eee 8e ee eeee eeeeeeeeeee eee eeeeeeeeeeee ee eeeeeee. Mee eeeeeee eee eeeeeeeee ee MM8Me8 eee eee eeeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeee eee eeeeee eeee eee eeeee, eeeee (MeMM8) eee 88eee, eee eeee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, MM8Me8/eeeeee 8:8) eeee eee eeeeeeeeee ee e eeee eeeeee eee; eeeee: 888ee (88%); MM ­ν̃M=M=M: 8888ee8.

References


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