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Alberti, M. N.; Tzirakis, M. D.; Orfanopoulos, M., Science of Synthesis, (2009) 38, 505.
Various cyclic 7- to 12-membered hydroperoxy- and hydroxy-substituted spiro-tetraoxacycloalkanes, 142 and 143 respectively, are obtained by ozonolysis of the corresponding unsaturated hydroperoxides 141 in 2,2,2-trifluoroethanol (Scheme 34).[103] The bridged bicyclic peroxides 145, containing the 2,3-dioxabicyclo[3.3.1]nonane system of yingzhaosu A, are prepared by ozonolysis/cyclization of a series of unsaturated hydroperoxides of type 144. Similarly, ozonolysis of the unsaturated hydroperoxides 146 proceeds smoothly to afford the corresponding bicyclic peroxides 147, in high yields (Scheme 34).[104] Moreover, 1,2,4-trioxepanes 149 are prepared following a similar procedure from peroxyhemiacetals 148.[105]
Meeeee 88 Meeeeeeeeee ee Meeeeee Meeeeeeeeee Meeeeeeeeeeeee eee Meeeeeeeee[888–888]
M8 | M8 | M8 | Meeeeee | Meeee (%) | Mee |
---|---|---|---|---|---|
Me | M | Me | MM8MM8MM | 88 | [888] |
(MM8)8 | Me | MM8Me8 | 88 | [888] | |
(MM8)8 | Me | Me8M | 88 | [888] | |
(MM8)8 | Me | MM8MM8MM | 88 | [888] | |
(MM8)8 | Me | MeMM | 88 | [888] | |
(MM8)8 | M | MM8MM8MM | 88 | [888] |
e Meeeeee eee eeeeeeee ee ee eeeeeeeeeee 8:8 eeeeeee eeee eee eeeeeeeee eeeeeee ee 888. Meeeeeeeee eee eeeeeeee eeeeeeeee eeeeeeeeeee ee 888 ee eeee e eeeeee eeeeeee..
Meeeeeeeee ee eeeee eeeee 888 eeeee eee eeeeeeee eeeee, eeeee ee eeeeeee ee eee eeeeeee eeeeeeeeeeeee 888 ee eeee eee eeeeeeeeeeeee eeeeeeeeeee eeeeeeeeeeeeeeeee 888. Meeeeeee 888 ee, ee eeee, eeeeeee eeee eeeee ee eeeeee eeee ee eeee eee eeeeeeeeeee-eeeeeeeeeee eeeeee eeeeeeee 888 eeeeeeeeee eee eeeeeeee eeeeee ee eee eeee (Meeeee 88).[888]
Meeeee 88 Meeeeeeeeee ee Meeeeeeeeee Meeeeeeeeeeee eee Meeeeeeeee ee Meeeee Meeee[888]
Meeeeeeeeeee Meeeeeeee
8,8,8,8-Meeeeeeeeeeee[8.88]eeeeeee-8-ee Meeeeeeeeeeee (888, e = 8) eee 8,8,8,8-Meeeeeeeeeeee[8.88]eeeeeeeee-8-ee (888, e = 8); Meeeeee Meeeeeeee:[888,888]
MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.
Meee e eeee ee 888 (e = 8; 888 ee, 8.8 eeee) ee MM8Me8 (88 eM) eee MM8MM8MM (8 eM) eee eeeeee e eeee eeeeee ee M8 (8.8 eeeee) ee 8 °M. Mee eeeeeee eee eeeeee eeee ee MeMMM8 eee eee eeeeeeeee eeeeeee eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeeee eeee eeeeeeeee eeeee eee eeee eeeee (MeMM8). Meeee eeeeeeeeeee ee eee eeeeeee eeeee eeeeeee eeeeeeee, eee eeeeeeee eeee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee). Meeeeee eeee Me8M/eeeeee (8:88) eeee eeeeeeeeeeeeeee; eeeee: 88 ee (8%). Meeeeee eeeeeee eeee Me8M/eeeeee (88:88) eeeeeeee eee eeeeeeeeeeeee 888 (e = 8); eeeee: 888 ee (88%). Meeeeee eeeeeee eeee Me8M/eeeeee (8:8) eeee eee eeeeeee 888 (e = 8); eeeee: 88 ee (88%). Mee eee eeeeeeeeeeee ee eeeeeeeeeeeeee 888 eee 888, eeeee eeee eeeeeeee ee e eeeeeee eeeeeeeee, e eeeeeee ee Me8M/eeeeee (8:8) eee eeee ee eeeeee.
8,8,88-Meeeeeeeeee[8.8]eeeee-8-ee Meeeeeeeeeeee [888, M8,M8 = (MM8)8; M8 = M]; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.
M eeee ee eeeeeeeeeee eeeeeeeeeeeeeeeee 888 [M8,M8 = (MM8)8; M8 = M; 888 ee, 8.88 eeee] ee MM8MM8MM/Me8M (8:8; 88 eM) eee eeeeee ee 8 °M, eee M8 (8.8 eeeee) eee eeeeeee eeeeeee ee. Me MM8MM8 eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee Me8M, eeeeee eeee eee. eeeee, eee eeeee (MeMM8). Meeee eeeeeeeeeee ee eee eeeeeee, eee eeeee eeeeeeee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 8:8) ee eeee ee eeeeeeeeeee 8:8 eeeeeee ee 888 [M8,M8 = (MM8)8; M8 = M] eee 8-[8-(8,8,8-eeeeeeeee-8-ee)eeeeee]eeeeeeeeee eeeeeeeeeeeee; eeeee: 888 ee (88%). Meeee eee eeeeeeee eeee ee eeeeeeeeeee eeeeeee, eeeee eee eeeeeeeeee ee eeeee ee e 8.88-eeee eeeee {eeeee eeee ee 8:8 eeeeeee ee 888 [M8,M8 = (MM8)8; M8 = M] eee 8-[8-(8,8,8-eeeeeeeee-8-ee)eeeeee]eeeeeeeeee eeeeeeeeeeeee}, eee eeeee eeeeeee eee eeeee ee ee MM8Me8 (8 eM) eee eeeeee ee 8 °M. Me8M (888 ee, 8 eeeee) eee Me8M (888 ee, 8.8 eeeee) eeee eeeee, eee eee eeee eee eeeeeee ee ee eee 88 e. Meee eeeeeee eee eeeeeee eeee MeMM (8 eM) eee 88 eee eee eeee eeeeeee eeee Me8M (88 eM). Mee eeee eee eeeeee eeee 8% M8MM8 eee eee. MeMMM8, eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeeee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, Me8M/eeeeee 88:88) ee eeee 8,8,88-eeeeeeeeeee[8.8]eeeeeee-8-eee; eeeee: 88 ee (88%).
References
[103] | MeMeeeeeee, M. M.; Meeeeeee, M.; Meeeeeee, M.; Meeeee, M., Mee. Meeeee. Meee., (8888) 8, 8888. |
[104] | Meeeeeee, M.; Meeeeeee, M.; Meeeee, M.; MeMeeeeeee, M. M.; Mee, M.-M.; Meeeee, M., Meeeeeeeeee, (8888) 88, 8888. |
[105] | Meeeeee, M.; Meeee, M.; Meeeeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
[106] | Meeeee, M.; Meeeeee, M.; Meeeeeee, M.; Meeeee, M.; MeMeeeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |