You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via43.8.2.1.6.2 Variation 2: Alkynes by Retro-Diels–Alder Reaction
Please login to access the full content or check if you have access via
Krueger, A., Science of Synthesis, (2008) 43, 494.
Retro-Diels–Alder reactions can also be used in principle for the synthesis of alkynes. However, the synthesis of the starting materials is in general complicated and the fragmentation gives rather uneconomic byproducts. In many cases the retro-Diels–Alder reaction is therefore less favorable than other synthetic methods leading to the same acetylenic compound (see Houben–Weyl, Vol. 5/2a, p 265). In some cases, however, highly reactive functionalized alkynes are accessible by a retro-Diels–Alder reaction (Scheme 34).[114–118] These products are then mostly used as efficient dienophiles in further Diels–Alder reactions (see Houben–Weyl, Vol. 5/2a, p 265).
Meeeee 88 Meeeeeeee ee Meeeeee ee Meeee-Meeee–Meeee Meeeeeeee[888–888]
M8 | M8 | M8 | M8 | M8 | M8 | Meeeeeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|---|---|---|
MM | MM | MM8Me | MM8Me | M | 888–888°M, 88 eee | 88 | [888] | |
MMMe | MMMe | eeeeee eeee, eeeeee eeeeeeeee (8 eeeee), 888–888°M, 8 e | 8–8 | [888] | ||||
M | M | M | M | MM8 | Me(MM8)8Me, eeeeeee, 88°M, 8 e | –e | [888–888] |
e Meeeeeee ee MM eeee.
Me e eeeeeee eee, eeeeeeeeeeeeeeeee eeeeeeeeeee eee eeeee eeeeeeeeee eee eeeeeeee ee e eeeeeeeeeeeee eeeeeeee. Meeee eeeeeeeeeeeeeee eee ee eeeeeeee eeeeeeeeeeeeeee ee eeeeeeeee; eeeee eeeeeeeee eee, eeeeeee, ee eeeeeee (eee Meeeee–Meee, Mee. 8/8e, e 888).
References
[114] | Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[115] | Meeee, M.; Meeeee, M., Meee. Mee., (8888) 88, 8888. |
[116] | Meeeeeee, M. M.; MeMeee, M. M., Meeeeeeeeee Meee., (8888), 888. |
[117] | Meeeeeee, M. M.; MeMeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
[118] | Meeeeeeee, M.; Meeeeee, M.; Meeeee, M., Meee. Mee. Meee. Me., (8888), 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.