You are using Science Of Synthesis as a Guest.
Please login to access the full content or check if you have access via35.1.4.1.2 Method 2: Reaction with Hypochlorous Acid
Please login to access the full content or check if you have access via
Pfeiffer, W. D., Science of Synthesis, (2007) 35, 174.
The reaction of hypochlorous acid with 1-methylcyclohex-1-ene (7) in dichloromethane affords 1-chloro-2-methylenecyclohexane (8) and 6-chloro-1-methylcyclohex-1-ene (9) in 60% combined yield and 25% of 2-chloro-1-methylcyclohexan-1-ol (10) (Scheme 4).[13] Similarly, citral (11, X = CHO), methyl geranate (11, X = CO2Me), geraniol (11, X = CH2OH), and geranyl acetate (11, X = CH2OAc) react to give the corresponding allylic chlorides 12 in 60–80% isolated yields. α-Ionone (13) gives a mixture of the allylic chlorides 14 and 15 with hypochlorous acid.[14] 2-(Chloromethyl)-4,4-dimethylpent-1-ene is obtained from 2,4,4-trimethylpent-1-ene in 46% yield.[15]
Meeeee 8 Meeeeeeee ee Meeeeee eeee Meeeeeeeeeee Meee[88,88]
Meeeeeeeeeee Meeeeeeee
Meeeeee Meeeeeeee, e.e. 8, 8, eee 88; Meeeeee Meeeeeeee:[88,88]
Mee eee eee eeeeee eeeee eeee e eeeeee ee 8–8 e ee e eeeeeee ee 88% Me(MMe)8 (88 eeee) eee M8M (88–88 eM), eee eeeeee (88 eeee), eee MM8Me8 (888 eM). Mee eeeeeeeee eeeee eeee eeeeeee ee eeeeeeeeee, eee eeeeeee eeeee eee eeeeeeeee, eee eee MM8Me8 eee eeeeeee ee eeeee eee eeeeeee; eeeee: 88–88%.
References
| [13] | Meeee, M. M.; Meeee, M. M.; Meeeeee, M.; Meeeee, M.; Meeeeeee, M.; Meeeee, M.; Meeeee, M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 888. |
| [14] | Meeee, M. M.; Meeeeeee, M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [15] | Meeeee, M.; Meeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8/8e, 888.
Return to Top