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Abell, A. D.; Edmonds, M. K., Science of Synthesis, (2009) 46, 35.
Ylides that contain a formyl substituent will react with an aldehyde or ketone to produce a 1,3-enal or 1,3-enone (e.g., 31) (Scheme 21). The addition of a second ylide to the 1,3-enal or 1,3-enone in situ can result in a second Wittig reaction to give a 1,3-diene. Thus, sequential addition of 2 equivalents of (triphenylphosphoranylidene)acetaldehyde to aldehyde 30 gives the corresponding E,E-dienal 32 (Scheme 21).[30]
Meeeee 88 Meeeeeeeee Meeeee Meeeeeeee ee e 8,8-Meeee[88]
Meeeeeeee, eee eee ee eee eeeeeeeee eeeeee eee eeee eeeeeee 8,8-eeeeee eeeeeeee eeee eeeeeee eeeeeeeeeee ee ee e eeeeeeeeee eee-eee eeeeeeee eeeeeeee eeee eeeeeee eeeeeeeeeeeeeee eeeee eeeeeeeee(MM) eeeee ee eeeeeee, e.e. ee eeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeeeeee Meeeee Meeeeeeee ee Meeeee eeee Mee Meeeeeeee Meeeeeeeee Meeeee[88]
M eee-eee eeeeeeeee ee 8,8-eeeeee eee eeee ee eeeeeeee ee eeeeeeeeee eeeeeeee ee eee eeeeee ee ee eeeeeeee eeeeee ee ee eeee eeeeeeeee ee α-eeeeeee eeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee eeeeeeee eeeee eeeeeeeee(MM) eeeee (Meeee 8).[88]
Meeee 8 Meeeeeeeee Meeeeeee ee Mee Meeeee ee ee Meeeeeee Meeeee Me Meee[88]
Meeeeeee Meeeeeee | Meeeeeeeee | Meeeeeee | Meeee (%) | Mee |
---|---|---|---|---|
MeMM8MM | 8. MeM8 (88 eeeee), Me8M=MMMMM, eeeeeee, ee, 8 e 8. Me8M=MMMMMe, 8 e |
88 | [88] | |
MeM8MMM8MM | 8. MeM8 (88 eeeee), Me8M=MMMMM, eeeeeee, ee, 8 e 8. Me8M=MMMM8Me, 8 e |
88 | [88] | |
8-M8MM8M8MM8MM | 8. MeM8 (88 eeeee), Me8M=MMMMM, MMM, eeee, 88 e 8. Me8M=MMMM8Me, eeee, 88 e |
88 | [88] | |
8. MeM8 (88 eeeee), Me8M=MMMMM, eeeeeee, eeee, 88 e 8. Me8M=MMMM8Me, eeee, 88 e |
88 | [88] |
e Mee eeeeeeeee eeeeeeeee eeee eeeeeee >88% ee eee M,M-eeeeeee
Meeeeeeeeeee Meeeeeeee
8,8-Meeeeee 8-Meeeee (8M)-Meee-8,8-eeeee-8,8,8-eeeeeeeeeeeeee (88, M8 = MMe); Meeeeee Meeeeeeee:[88]
M eeeeeee ee eeeeeee eeeeeeeeeeeeeee (888 ee, 8.88 eeee), Me8M=MMMMM (888 ee, 8.88 eeee), eeeeeeeee MeM8 (888 ee, 88.8 eeee), eee eeeeeeee 8-Å eeeeeeeee eeeeee (8.8 e) ee eeeeeee (8 eM) eee eeeeeee ee ee eee 8 e. Me8M=MMMM8Me (888 ee, 8.88 eeee) eee eeee eeeee, eee eee eeeeeee eee eeeeeee eee 8 e, eeeeeeee eeeeeee e eee ee eeeeee eee, eee eeeeeeeee eeee Me8M (88 eM). Mee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 8:8); eeeee: 888 ee (88%).
References
[30] | Meeee, M. M.; Meee, M. M.; Meeeee, M. M.; Meeeeee, M. M.; Meee, M. M.; Meeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
[31] | Meee, M.; Meeeee, M. M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |