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Purchase, R.; Sainsbury, M., Science of Synthesis, (2009) 40, 365.
When a quaternary ammonium salt 1 bearing an electron-withdrawing group Y, directly bonded to a methylene substituent, is treated with a strong base, such as sodium amide in liquid ammonia, deprotonation takes place and the nitrogen ylide 2 that is formed rearranges so that one or other of the other groups on the electron-deficient nitrogen atom migrates to the carbon adjacent to the group Y to form a tertiary amine 3. This process is known as the [1,2]-Stevens rearrangement as it involves a [1,2]-sigmatropic change (Scheme 1).[3–5]
Meeeee 8 Mee Meeeeee Meeeeeeeeeeee[8–8]
Meeeeeeee, eee eeeeeeee-eeeeeeeeeee eeeee M ee ee eeee, eeeee, ee eeee eeeeeeee, eee eeeee eee eeeeeeee eeeee ee eeee eeeeeeeeee eeeeeeee, eeeee eeee eee eeeeeeee eeeeee eeeeee, ee eeeeeeee.[8] Meee “eeeeeeeeeee” eeeeeeeeeeeeee eee eeeeeee eeeeeee eeeeeeeeee ee eeeeeeeeeee eee eeeeeeeee, ee eeeee eeeeeee eee ee eeeeeeeee ee eeeeeee e eeeeeeeeeeee eeeeeeeeee eeeeeee eeeeee eee eeeeeeeee ee eeeee; eee eeee eeeeeeeeee, eeeeeeeeeeee eeeee ee ee eeee.[8] Meeeeeeee, ee eee eeeee eeee ee eee Meeeeee eeeeeeee eeeeee eeeee eeee eeeeeeeeee eeee eee eeee eee eee eeeeeeeeeeee ee eeeeeeee eeee eeeeeeeee eeee e eeeeeeeeeeee eeeeeeeeee eee eeeeeee, ee ee eeeee Meeeeee eeeeeeeeeee eeeeeee eeeeeeeeeee eeeeeeeeeeeee.[8,8] Meeeeeeee eeeeee eeeeeee eeeee, eeeeee, eeeeeeeeeeeeee (eeeeeeeeee), eeeeeeee, eee eeeeeeeeeeeeeee eeeeeeeee eeeee eeeeee, eee ee ee eeeee eeee eee eeeeeeeeeeeee ee e eeeeeeeee eeeee, eeee eeeeeee ee eee eeeeeeeeee eeee eeeeeeee eeeeeeee, ee eeeeeeee ee eee eeeeeeee eeeee eeeeeee.[88,88] Meeeeeeee ee ee eeee eeeee ee eeee eee ee eeee eeeeeeee.[88,88]
Mee eeeeeeeee ee eee Meeeeee eee eeee ee eeeeeee eeeeeeeee eeeeeeee ee ee eee eeeeeee ee eeeeeeeeeee eeeeeee eeeee ee e eeeeee eeeeeeeeeeeeee ee eee eeeeee ee eeeeeeeee eeeeeeeeeeee eeeeeee eee eeeeeeeee.[88] Meeeee, eeeeeeee eeeeeee eeeeeeeeee eeee eeee eeeeeeee ee eeeeeee eee Meeeeee eeeeeeeeeeeee, eeeee eeeeeeeee ee eee eeeeeeeeeeee ee eeeeeee eeeeeeee ee e eeeeeeee-eeeeeeeee eeeeeeee, eee eeeeee ee eeeeeeee eeeeeeee eeeeeeeee eeeeeeee ee e M—M eeee ee eee eeeeeeee eeeee eeeeee ee eeee eee eeee eeeeee eeeeee-eeeeeeee eeeeeee eeeeeeee e eeeeeee eee e eeeeeee eeeeee ee e eeee eeeeeeee eeeeee e eeeeeee eeee. Mee eeeeeeee eeee ee eeeeeeee ee e eeeee eeeeeeeeeee ee eeee eee Meeeeee eeeeeee eeeeeee ee eeeeeee [8,8]-eeeeeeeeeee eeeee.[88–88] Meeeeee, e eeeeeeeeeee eeeeeeeeeeee ee eeee e Meeeeeee–Meeeee [8,8]-eeeeeeeeeee eeeeeeeeeeeee, e eeeeeeee-eeeeeee eeeeeee (Meeeee 8),[88,88] eeeeeeee eeee eee Meeeeee eeeeeeeeeeeee eeee eee ee eee eeeeee ee eeeeeeee ee eeeeee (ee eeeee). Mee eeeeeee, eeeeeeeeeeeeeeeeeeeeeee eeeeee (8, M8 = M8 = Me; M = M) eeeeeeeeee eeee eeeeeee eeee eeeeee eeeee ee eeeeee eeeeeee ee eeeeeee M,M,8-eeeeeeeeeeeeeeeeeeee (8, M8 = M8 = Me) ee 88–88% eeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeee–Meeeee Meeeeeeeeeeee
Meee eeeeeeeeeee eeeeeee [8,8]- eee [8,8]-eeeeeeeeeee eeeeeeeeeeeeee ee eeeeeeeeeee eeee eeeeeeeeeeeeeeeeeeeeeeee eeeeeee ee eeeeeee eeee eeeeeeeeeeeee ee eeee eee Meeeeee eeeeeee, M,M-eeeeeeee-8,8-eeeeeeeeeeeeeeeeee (8), eee eee Meeeeeee–Meeeee eeeeeee, M,M-eeeeeeee-8-eeeeee-8-(8-eeeee)eeeeeeeeeee (8), eee eeeeee; ee eeeeeeee ee eeeeeeeeeee eeeeee eee Meeeeee eeeeee eeee eee Meeeeeee–Meeeee eeeeeeeeeee (Meeeee 8).[8]
Meeeee 8 Meeeeeeeeee eeeeeee Meeeeee [8,8]- eee Meeeeeee–Meeeee [8,8]-Meeeeeeeeee Meeeeeeeeeeeee[88–88]
Meee eee eeee eeeeeee eeeee eeeee eee eeeee ee eeeeeeeeeeeeee eee e eeeeee ee eeeeeee eee eeeeeeeee.[88,88–88] Mee eeee eeeeeeeee eeeeeeeeeee ee Meeeeeee–Meeeee eeeeeeeee, eeeee eeeeeeeee eeeeeeeeee, ee ee eeeeeeeeeeee eeeeeeeee eee, eeeeeeeeeeeeee, eeeee eee eeeeeeee eeeeeeee ee eeeeeeeeeeee eeee eeeee. Meeeeeeee ee eeee e eee eeeeeeeeeeeee ee eeeee eeee,[88–88] eee eeeeee eee ee ee eeeee ee eee eeeeee eeeeeeee eeeee eeeee, eeeee eeee eeee eeeeee eeeeeeeeee ee eee eeeeeeeeeee eeeeeee eee eeeeeeeee. Me eeeee ee eeeeeeeeeeeee eeeeeee eeeeeeeeeee Meeeeee eee Meeeeeee–Meeeee eeeeeeeeeeeeee eeeee ee ee eeeeeee eeee ee eee eeeeeeeee eeeeeeee/eeeeeeeeee eeeeeeee eeeeeeee, eee eeee eee eeeeeeeee eeee eeeeeeeee. Mee eeeeeee, eee eeeeeeeee ee e eeeeee ee eeeeeeeeeeeeee(eeeeeeeeeee)eeeeeeee eeeee 8 eeee eeeeee eeeeee eeeee ee eeeeee eeeeeee ee 88–88°M, ee eeeeeeeeeeeee ee eeeeee ee 8–8°M, eeeee ee eeeeeeee ee Meeeeee eee Meeeeeee–Meeeee eeeeeeee 8–88 ee eeeeeee eeee eeeeee eeee eee eeeee eeeee eee eee eeeeeeeeee (Meeeee 8).[88] Meeeeee eeeeeeeee ee eee eeeeeeeeeee eeeeeeeeee eeeee 88, eeeeeeeee eeeeee eeeeeeee ee eeeeee eee M—Me eeee eee ee eeee eeeeeeeeeeee eeeeeeee eeeeee, eeee eeee eeeeee eeeeeeeeeee eee eee eee Meeeeeee–Meeeee eeeeeeee 88 eeeeeeeeeee eeee eee Meeeeee eeeeeeee 88 (Meeeee 8).[88–88]
Meeeee 8 Meeeeee eee Meeeeeee–Meeeee Meeeeeee eeee eee Meee-Meeeeeee Meeeeeeeeeeeee ee Meeeeeeeeeeeee(eeeeeeeeeee)eeeeeeee Meeee[88]
Meeeee 8 Meeeeeeeeee ee eee Meeeeeeeeeeeee ee Meeeeeeeeeeeee(eeeeeeeeeee)eeeeeeee Meeee Meeee Meeeee Meeeeeee Me Meeeee eee M—Me Meee[88–88]
e Meee M = Me, MM ee eeeee ee eee MeM/MMMM eeeeeee.
Meeeeeeee, eeee 8-eeee-8-eeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeee-8-eee eeeeeee 88 eee eeeeeee eeee eeeeeeee eee ee eeee eee, eeeeeeeee eeeeeeeeeeeeee ee eeee 8-eeee-8-eeeeeeeeeeeeeeeee 88 eeeee (Meeeee 8).[88]
Meeeee 8 Meeeeeeee ee 8-Meee-8-eeeeeeeeeeeeeeeee[88]
Me eeeeeee eeee, eeeeeee, eeeeeeeee ee eee eeeeeeeeee eeeeeee 88 eeee eeeeee eeeeeeee ee eeeeeeeeeeeeeeeee ee eeee eeeeeeeeeee eeeeeeee eee eeeeeeee eeeee 88 ee 88% eeeee eeeeeee e [8,8] eeeee, eeeeeee eee eeeeeeeeee eeeeeeeeeeeeeeeeeee 88 eeeeeee e 8:8 eeeeeee ee Meeeeeee–Meeeee eee Meeeeee eeeeeeee 88 eee 88, eeeeeeeeeeee (Meeeee 8), ee eeee ee e eeeee eeeeeeee ee 8,8-eeeeeeeeeeeeee.[88]
Meeeee 8 Meeeeee eeeeee Meeeeeee–Meeeee Meeeeeeeeeeeee Meeee Meeeee Meeeeeee Me Meeeee eee M—Me Meee ee Meeeeeeeeeeeeeeeee Meeeeeeeee Meeee[88]
Meeeee, eeeeeeeeeeee eeeeeeeeeeeee eee eeeeeeeee ee eeeeeeee ee Meeeeeee–Meeeee eeeeeeeeeeeee eeeeeeeee; eee eeeeeee, eeee 8-eeee-8-eeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeee eeeeeee 88 eee eeeeeee eeee eeeeee eeeeeeee, eeee eeeeee ee 8-eeeeee-8,8,8,8,8,8-eeeeeeeee-8M-8-eeeeeeeeeeee 88 eee eeeeee. Meee eeeeeeeeeeeee eeee eeeeeeee eeeeeeeeee ee ee eeeeeeeee ee eeee eee, ee eeee, eeeeeeeee eeee 88% eeeeeeeee eeeeeeeee ee eeeeeee ee eeeeeeee ee eeeeeeeee eeee eeee eee eeeeeeee 8-eeeeee-8,8,8,8,8,8-eeeeeeeee-8M-8,8-eeeeeeeeeeeeeee 88 (Meeeee 8) eee, eeee eeeee, eeeee eeeeeeeee eee ee eeeeee eeeeeeeee eee eeeeeee eeeee ee 8°M.[88] Meeeeee eeeeeeee ee eeeeeeee eeee 8-eeee-8-eeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeee eeeeeee 88 eee eeeeeee ee eeee eee, eee ee eeee eeeee eee eeeeeeeeeeeee eeeeeee eeeeeeee 88 eee eeeeeeeeeee ee eeeee eeeeeeeeee eeeeeee 88, eeeeeeee eeee eeee eeee-eeeeeee eeeeeeee 88 (Meeeee 8).[88]
Meeeee 8 Meeeee Meeeeeeeeeeee eeee eee Meeeeeeeeeeeee ee 8-Meee-8-eeeeee-8-[(eeeeeeeeeeeeee)eeeeee]eeeeeeeeeeee ee -eeeeeeeeeeee Meeeeee[88,88]
Meeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeee eeeeeee Meeeeee eee Meeeeeee–Meeeee eeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeeeee eeee M-[(eeeeeeeeeeeeee)eeeeee] eeeeeeee eeeeeeeeeeee ee eeeeeee eeee eeeee eee eeeeee eeeeeeee. Me eee eeee ee eee 8,8,8,8,8,8-eeeeeeeee-8M-8-eeeeeeeeeee 88, eee eeeeeee, eee [8,8]-eeeee eeeeeee 88 ee eeeeeee eeee eee 88-eeeeeeeee-8-eeeeeeeeee[8.8.8]eeeeeee-8(88),88-eeeee 88, eeeeee ee e Meeeeeee–Meeeee [8,8]-eeeeeeeeeee eeeeee, eeee e 88:88 eeeeeee eeeee. Meeeeee, ee eee eeee eeee ee eee eeeeeeee eeeeeeee eeeeeeeeee, eee Meeeeee eeeeeee eeeeeee eeee eeeeeeee, eee eee 8,8,8,8,8,8-eeeeeeeee-8-eeeeeeeeeee 88 eee eeeee ee eee eeeeeeeeeeeee eeeeeeee 88/88/88 (ee eeeeeee eeee MMM eeeeeeeeeeee ee eee eeeee eeeeeeee eeeeeee) ee 88:88:88, eeeeeee eee eee eeeee eeeeeeeee 8,8,8,8-eeeeeeeeee-8M-8-eeeeeeeeeee 88 eee eeeee eeeeeeee 88, eeeeee ee e Meeeeeee–Meeeee eeeeeeeeeeeee, eeeeeeeeeeee eeee eee Meeeeee eeeeeeeeeeeee eeeeeee 88 ee e eeeee ee 88:8 (Meeeee 8).[88]
Meeeee 8 Mee Meeeee ee Meee Meee ee eee Meeeeee ee Meeeeee eeeeee Meeeeeee–Meeeee Meeeeeeee ee Meee Meeee-Meeee Meeeeeeeeeee[88]
Meeeeeee eeeeee eee eeee eeeeee ee eeeeeeeee eeeeeeee eeee eeeeeeee eeeeee eeeee eeeeeeeeee eeee eeeeeeeeee eee ee eeeee ee 8888 ee eee eeeeeeeeeee eeee eeeeeeeeeee ee eee eeeeeee 88 eeee M,M-eeeeeeeeeeeeeeeeeee eeeee 8-eeeeee-M,M-eeeeeeee-8M-eeeeeee-8-eeeee (88) ee 88% eeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee 8-Meeeee-M,M-eeeeeeee-8M-eeeeeee-8-eeeee eeee 8-Meeeeeeeeeeee eee M,M-Meeeeeeeeeeeeeeeeee[88]
Me ee eeee eeeeeeee eeee eeeeee M,M-eeeeeeeeeeeeeeeee eeeeee eeee eee eeeeeee 88 (eeee eee eeeeeeeeee ee eeeeee 8-eeeee-8-eeeeeeeeeeeee ee eeeeeeeeeeeee) ee eeee eee eeeeeeee eeeee 88, eeeee eeee eeeeeeeee e Meeeeee eeeeeeeeeeeee ee eeeeee eeeeeeee M,M-eeeeeeee-8-eeeeeeeeeeeeeee (88) (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee Meeeee M,M-Meeeeeee-8-eeeeeeeeeeeeeee[88]
Meeee eeee eeeeeeeeeeee eeee eeeeeeee, eeeeeeee eeee eee eeeeeee ee eeeeeeeeeeeee eeeeeeeeeeeee ee eeeee eeeeeeeee, eeeee eeee eeeeeee eeeeeeeee eeee eeeeee eeeee eeeeeeeeee eee eee eeeeee eeeeeeeee.[88–88] Meeeee eeeeeee eeeeee ee eeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeee eee eeeeeeee ee eeee eeee ee eeee eee, eee eeeeeee, eeeeeeeeeeeeee eeeeeeeee eeeeeee eee eeeee eeeeeee 88 eee eeeeeee eeeeee 88 ee eee eeeeeeee ee eeeeee ee eeeeeee ee eeeeee eeeee eee B-eeeeeeeee 88 ee eeeeeee eeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee B-Meeeeeee Meeeee[88]
e Mee eeeeeeee eeeee eeeeeeee eee eee eeeeeeee. Meeeeeee eeeeee-8,8,8-eeeeeeeeeeeeee eee eeeeeeee ee 88% eeeee.
e Mee eeeeeeee eeeee eeeeeeee eee eee eeeeeeee. Meeeeeee eeeeee-8,8,8-eeeeeeeeeeeeee eee eeeeeeee ee eeeeeeeeeeee eeeee.
Me ee eeeeeeeeeeeeee eeeeeee ee eeee eeee ee eeeeeeeee, eeeeeee eeeeeee(MM) eeeeeee eeeeeee eee eeeeeeeee ee eeeeeeee eeee 8-eeeee-8-eeeeeeeeeee-8-eeee 88, eeeee eeee eeeeeee eeeeeeeeeee ee eeee eee eeeeeeeee-8-eeee 88 (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeee ee Meeeeeeee-8-eeee eeee 8-Meeee-8-eeeeeeeeeee-8-eeee[88,88]
Meeeeee eeeeeeeeee eeeeeee 8-eeeeeeeeee eeeeeeeeeeeeeee 88 eeee eeeeeeeee-8-eeee 88 eee 8-eeeeeeeeeee eeeeeeeeeeeee 88 eeee 8,8-eeeeeee-8M-8,8-eeeeeeeeee-8-eeee 88 (Meeeee 88).[88,88]
Meeeee 88 Meeeeeeee ee Meeeeeeee-8-eeee eee 8,8-Meeeeee-8M-8,8-eeeeeeeeee-8-eeee[88,88]
Meeeee a-eeeee eeeeeee 88 eee ee eeeeeeee eeee eeeee eeeeeee 88 ee eeeee-eeeeeeeee eeeeee eeeeeeee eeeee eeeeeeeeee eee [8,8]-eeeeeeeeeee eeeeeeeeeeeeee ee eee eeeeee 88, ee eeeee eeeeeeeeeee (Meeeee 88).[88] Meeeee-eeeeeeeee eeeeeeeee ee eee-eeeeeee eeeeeeee eeeeeee eeeeeeee eeeeeeee eeeee eee eeeeeee eeee eee eeeeee; eeeeeee, eeee eeeeeeeeee eeeeeee eee eeeeeeee eeee eeeeeee ee eeeeee ee eee eeeeeee eee eeee eeeeee eeeeee(MM) eeeeeeeeeeeeeee ee eeeeeee(MM) eeeeeee eee eee eeeeeeeee.[88]
Meeeee 88 Meeeeeee Meeee–Meeee Meeeee Meeeeeeeeeeeee[88]
Meeeeee eeeeeeeee ee eeee eeeeeeee eee eee eeeeeeeeeeee ee eeeee eeee eeeeeeeeee,[88] eee e eeeeee ee eee eee ee eeeeeeee ee eee eeeeeeeee ee eeeee eeee eeeeeeeeeee ee eeeeeeeee.[88] Meeeeee eeeee eeeeeeeeee, eeeeeeeee eee eee ee eee Meeeeeeee eeeeeeee ee eeeeee eeeeeeee eeeeee eeee eeeeeeee eeeeee, eee eeeeeeee. Meee, ee eee eeee ee eee eeeeeee 88, eeee e eeeeeeee eeeeeee eee eeeee eeeeee eeeeeeeeeeeeeeeee eee 8,8′-(eeeeeeeeeeeee)eeeeeeeeeeee eeeee e eeeeee ee eeeeeeee eeeeeeeeeeeee eeee eeeeeeeeee eeee eee eeeeeeeeeee 88 ee eee eeee eeeeeee ee eeee eeeeeee eeeeeeeeeee e eeeeee eeeeeeeeeee–Meeeeee eeeeeeeeeeeee eeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee Me-eeee-eeeee 8-(Meeeeeeeee-8-ee)eeeeeeeeeeee[88]
Me e eeeeeeeeeeeee eeeeee ee eeeeeeee ee eee Meeeeee eeeeeeeeeeeee ee eeeeeeee eeeeee[88] eeeeeeee ee eeeee ee eee eeeee ee eeee eeeeeeeee, eeeeeeeeee eeee ee eeeeeeeeeee eeeeee, ee eee eeeeeeeee ee eeeeeeee eeeeeeeeee. Me eeeeeeee, eee eeeeeeeee ee eeeeeeeeeee eeeeeeeeeee eeee eeeeeeeeeeee,[88] eee eeeeeeeee ee eeeeeeeeeeeeee eeeeeeeeeeee eeee eeeeeeeeee,[88] eee ee eee eeeeeeeeeeee ee eeeeeeeeee[88] eee eee eeeeeeee eeee[88] eee eeeeeeeeeee ee eee eeee eeeee eeeeeee eeeeeeeeee. Me eee eeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeee eee Meeeeeee–Meeeee eee Meeeeee eeeeeeeeeeeeee, eee eeee-eeeeeeee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeee 88 eee eeeeeeee ee eeeeeee eee Meeeeeee–Meeeee eeeeeee 88 eeee, eeeee eeeeeeeeeeee, eeeee eeeeee eee eeeeeeee 88 e eeeeeeeee eeeeeeeee ee MMM-8 eeeeeee eeeeeeeeeeeee. Me eeee, eee eeeee eeeeeee ee eee Meeeeee eeeeeee 88, eeeee eeeeeeeeee eeeeeee eee eeeeeeee eeeeeeee ee eee eeee ee eee M,M-eeeeee 88 (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee e Meeeeeeee MMM-8 Meeeeee Meeeeeeeeeeee Meeeeeeee ee e Meeeeee Meeeeeeeeeeee[88]
Meee M8-eeeeee-M,M,M8-eeeeeeeeeeeeeeeeeeee (88, M8 = M8 = M) ee eeeeeee eeee eeeee eeeeeeeeee, ee eeeeeeeeeeeeeee eeeeeeeeee 88 ee eeeeee eeee ee eee eeeeeeee ee eeeeeeeeeeeee ee eeeeeeeeeeee eee eeeeeeeee e [8,8] eeeee ee eeeeee M,M,Ma-eeeeeeeeeeeeeeeeeeeeeeeeee (88, M8 = M8 = M), eeeee eeeeeeeeee. Meee eeee ee eeeeeeee ee eeeeeeeeeee ee e eeeeeeeeeee ee eeeeeeeee eeeeeeeeeee eee eeeeee eeeeeee eeee eee eeeeeee eeeee ee M,M,Ma-eeeeeeeeeeeeeeeeeeeeeeeeee eeeeeeee ee 88%; eeeeeee, eeeeee eeeeeee ee eeeeeeeee eee eeeeee eee eeeeeeeeeeee ee eeee eeee ee eeeeeeeee. Me eee eeee ee eee eeeeeeeee 88 (M8 = M; M8 = Me), eee eeeeeeeeeeeee eeeee 88 (M8 = M; M8 = Me) ee eeeeeeee ee e 8:8 eeeeeee ee eeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeee ee M,M,Ma-Meeeeeeeeeeeeeeeeeeeeeeeeee eeee eee Meeeeee Meeeeeeeeeeee ee M8-Meeeee-M,M,M8-eeeeeeeeeeeeeeeeeeeee[88]
Meeee eee eeeeeeee ee eeeee eee Meeeeee eeeeeeeeeeeee ee eeee eee eee eeeeeeeeee eeeeeeeee ee eeeee eeeee eee eeeeee eeeeeeee eeeeee,[88,88] eee eeeeeeeeeeee ee eee Meeeeeee–Meeeee ee e eeeeeeeee eeeeeee. Meeeeeeeeeee, eeeeeee eeeeeeeee eee eeeeeeeee ee e eeeeeeeeeee eeeeee; eeee, eeeee eee [8,8]-Meeeeee eeeeeeeeeeeee ee eee eeeeee eeeeeeee eeee 88 ee eeeeeee ee eee eeeeee ee eeeeee eeeeeeeee ee 8,8-eeeeeeeeeeeeee ee −88°M ee eeeeee eee eeeeeeeeee eeeeeee eeeee 88 ee e eeee eeee eeeeeeeeeeee eeeeee, e [8,8]-Meeeeeee–Meeeee eeeeeeeeeeeee eeeee eeeee eeee eee eeee ee eeeeeeeee eeee-eeeeeeee ee eeeeeeeeeeeeeee ee −88°M. Me eeee eeee eee eeeeeee ee eee eeee eeeeeee 88, eeeee ee eeeeee ee 88% eeeee eee eeee e eeeeeee eeee eeeeee ee eeeeee eeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeee Meeeeeeee ee Meeee Meeee eee Meeeee Meeeeeee Meeeee[88]
Me eeeeeeee, ee ee eeeeeeee ee eeeeee eee eeeeeeeeee [8,8]-Meeeeeee–Meeeee eeeeeeeeeeeee ee 8-eeeeeeeeeee M-eeeeeeeeeeeeee eeeee 88 ee eeeeee eee eeeeeeee M,M-eeeeeeeeeeeeeeeeee 88, eeeee eee (–)-8-eeeeeeeeeeeee eeeee (M8) ee e eeeeee eeeeeeeee (Meeeee 88).[88]
Meeeee 88 Meeeeeeeee Meeeeeee–Meeeee Meeeeeeeeeeeee ee 8-Meeeeeeeeee M-Meeeeeeeeeeeee Meeee[88]
[8,8]-Meeeeeeeeee eeeeeeeeeeeeee ee eeeeeeee eeeeee eeeeeee eee M-eeeee eeeee eee eeee eeeeeeeeeee[88–88,88–88] eee e eeeeeeeeeee eeeeeee ee eeee eeeeeeee-eeeeeee eeeeeeee ee eeeeeeee ee Meeeee 88. Mee eeeeeeee eeeeeeee e eeee-eeeeeeee eeeeeeeeee eeeee ee eeeee eee eeeeeee M—M eeee eee eee eeeeeeee M—M eeee eee eeeeee eeeeeeee. Meee eeeeeeeeeee eeeeeeeee eee eeeeeee eeeeeee eee MMMM ee eee eeeee eeeee eee eee MMMM ee eee M=M eeee (ee eeee eeeee). Me eeeeee eeeeeeeeeeeee ee eeee eeee ee eeee eeeeeeee ee Meeeee 88 ee eeeee eee a-eeeee eeeee 88 eeeeeeeee eeee M-eeeeeeeeeeeeeeee ee eee eeeeeeee ee eeeeeeeee eeeeeeeee eee eeeeeeeeeeeeeeeee ee eeee eee eeeeeeeeee eeeeeeee eeeee 88. Meee eeeeeeeeeeee eeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee eeeeeeeeeee eee eeeeeeeeeee eeeee eeeeeeeee eeeee eee eeeeeeeee ee eee eeee, eeeeeeeee eeeeeeeee, ee eeeeee eee eeeeeee eeeee 88 ee eeee e eeeeee eeee eeeeee eeeeeee ee eeeeeeeee eeee eee eeeeeeeeee ee eeee eeeeeeeeeeeee (Meeeee 88).[88]
Meeeee 88 [8,8]-Meeeeeeeeee Meeeeeeeeeeeee ee Meeeeeee Meeeee Meeeeee ee M-Meeee Meeee Meeeeeeeeee ee e Meeeeeeee ee e Meeeeee Meeee[88]
M [8,8]-eeeeeeeeeee eeeeee eeeeeeeee eeee eeeeeeeeeee eeeee eeeee eeee eee 8,8,8,8-eeeeeeeeeeeeeeeeeeee eeeeeeee 88 eee eeeeeee eeee eeeeee eeeeeee ee eeeeeeeee 8,8-eeeeeeeeeeeeeee. Me eeee eeee eee eeeeeeee eee eeeeee eee eee-eeeeeee 8-eeeeeeeeeeeee 88 eeee eee eeeeeee eeeeee 88 ee eeeeeeeeeee eeeeeeeeee, eeeeeeee eeee eee eeeeeeeeeee M8 ee eeeee eeee ee eee eeee eeeeeee (88% eeeee) (Meeeee 88). Me eeeee eeeeeeeee, eeee ee eeee eee eeeee M8 ee 8-eeeeeeeeeeeee, eeee eeee-eeeeee eee eeeeeee eeeeeeee eee eeeeee ee eeeeeeeeeeeee eeeee eeeeeee.[88]
Meeeee 88 Meee Meeeeeeeeee ee 8,8,8,8-Meeeeeeeeeeeeeeeeeee Meeeeeee[88]
Meeeeeeeeeee Meeeeeeee
8-Meeee-8-eeeeeeeeeeeeeeee-8-eee (88, M8 = Me; e = 8):[88]
M eeee ee eee a-eeeee eeeeee 88 (M8 = Me; e = 8; 888 ee, 8.88 eeee) ee eee eeeeeee (MMMMMMM: eeeeeeeeee) eee eeeee ee Me(eeee)8 (8.8 ee, 8.88 eeee) ee eee eeeeeee (88 eM) ee eeeeee, eeee e eeeeee ee ee. 8 e. Mee eeeeeeeee eeee eee eeeeee ee eeeeee eee e eeeeeee 88 eee, eee eeee eeeeee ee ee eeeeee e eeeeeee, eeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M) ee eeeeee e eeeeeeeee eeeeee; eeeee: 888 ee (88%).
(–)-8-Meeeeeeeeeeee (8M)-[8-(eeee-Meeeeeeeeeeeee)-8-eeeeeeeeeeee](eeeeeeeeeeeee)eeeeeee (88, M8 = MM8e-Me):[88]
M eeee ee eee eeeeeeee eeee 88 (M8 = MM8e-Me; 888 ee, 8.88 eeee) ee MMM (8.8 eM) eee eeeeee ee −88°M eee 8 M e-MeMM ee MMM (88 eM, 8.88 eeee) eee eeeee eeeee eee eeeeeee eee eeeeeeeee eeeee eeeee. Mee eeeeeee eee eeeeeee ee −88°M eee 8 e, eeeeee ee eee eeeee ee e eeeeeee eee-eeee eeee ee eee. ee MM8MM. Mee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M eee eee eeeeeeee eeeeeeee eeee eeeeee eeee eee. ee MeMMM8, eee eeee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Meeeeeeeeeee ee eee eeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeee/MeMMe 8:8 ee 8:8) eeee e eeeeeeeee eee; eeeee: 888 ee (88%).
References
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) 88/8, 888.
- 8.Meeeee-Meee, (8888) M 88e8, 8888.
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