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Kwiecień, H., Science of Synthesis Knowledge Updates, (2014) 4, 246.
2,3-Dihydrobenzo[b]furan-2-ols (e.g., 508) undergo dehydration to give benzo[b]furans (e.g., 509) on treatment with phosphoric acid,[381] concentrated sulfuric acid,[382] or 4-toluenesulfonic acid (Scheme 214).[383] The 2,3-dihydrobenzo[b]furan-2-ols are usually obtained via ozonolysis of 2-allylphenols (e.g., 507),[383] or by reaction of 2-hydroxybenzaldehydes with diazo compounds (Schemes 215 and 216).[384,385]
Meeeee 888 M 8-Meeeeeeee[e]eeeee eeee Meeeeeeeeee ee e 8,8-Meeeeeeeeeee[e]eeeee-8-ee[888]
Meeeeee eeeeeeeeeee eeeee eeeee[e]eeeee-8-eeeeeeeeeeee 888 eee eeeeeeee ee eeeeeeeeeee ee eeeee 8-eeeeeee-8,8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee 888 eeeee eeeeeeeeeeee eeeeeeee eeee.[888] Mee eeeeeeeee eee ee eeeeeeeeeee ee eeeeeeee ee eeeeeeeeeee 8-eeeeeeeeeeeeeeeeeeee 888 eeee eeeee eeeeeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeeeeeeeeeeeee eeee ee eeeeeee eeeee (Meeeee 888).[888]
Meeeee 888 Meeee Meeee[e]eeeee-8-eeeeeeeeeeee eee Meeeeeeeeee ee Meeee 8-Meeeeee-8,8-eeeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee[888]
Meeeeeeeeeeeeeeeeee eeeee[e]eeeee 888 ee eeeeeeee eee eeeeeeeeeee ee 8-(eeeeeeeeeeeeeee)-eeeeeeeeeee 8,8-eeeeeeeeeeee[e]eeeee-8-ee 888. Mee eeeeee ee eeeeeeee ee eeee eeeeee eeee eee 8-eeeeeeeeeeeeeeeeeee ee eeeee ee eeee eeeeeeeee 8-eeeee-8,8,8-eeeeeeeeeeeeeee eee eeeee eeeeeeeeeee ee ee eeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee e 8-(Meeeeeeeeeeeeee)eeeee[e]eeeee[888]
Meeeeeeee ee eeeee[e]eeeee-8(8M)-eee (88) eeee eeeeeeeeee eeeeeeee ee eee eeeeeeee ee eeeeeeeeeeeeeeeee eeeeeee eeeee 8-eeeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888) ee 88% eeeee (Meeeee 888).[888,888]
Meeeee 888 Meeeeeeee ee 8-Meeeeeeeeee[e]eeeee-8-eeeeeeeeeeee eeee Meeee[e]eeeee-8(8M)-eee[888]
Meeee[e]eeeee-8(8M)-eeee eee ee eeeeeeeee eeee eeeee[e]eeeeee eee eeeeeeeee ee eee 8,8-eeeeeeeeeeee[e]eeeee-8-eee eee eeeeeeeeee eeeeeeeeeee.[888–888] Mee eeeeeee, eeeee[e]eeeee-8-ee (888) eee ee eeeeeeee eeeeeeee eeee 8-eeeeeeeeeeee[e]eeeee-8(8M)-eee (888), eeeee eeeeeeeeee ee eee eeeee eeeee, eeeeeeee ee eeeeee eeeeeeeee eeee eeeeee eeeeeeeeeee, eee eeee-eeeeeeee eeeeeeeeeee eee eeeeeeeeeeee (Meeeee 888).[888]
Meeeee 888 Meeeeeeee ee Meeee[e]eeeee-8-ee eee Meeeeeeee ee 8-Meeeeeeeeeee[e]eeeee-8(8M)-eee[888]
Meeeeeeeee ee eeeee[e]eeeee-8(8M)-eeee (e.e., 888) eeee eeeeeeeeeee eeeee[e]eeeeee (e.e., 888–888) eee eeee ee eeeeeeee eee eeeee eeeeeeeeeeeeeee ee eee eeeeeeee eeeee (Meeeee 888).[888]
Meeeee 888 Meeee[e]eeeeee eeee Meeeeee Meeeeeeeeeeeeee ee 8-Meeeeeeeeeee[e]eeeee-8(8M)-eee[888]
Meeeeeeeeeee Meeeeeeee
8-[8-(Meeeeeeee)eeeeee]-8-eeeeeeeeeee[e]eeeee (888); Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeee eeeeeeeee eeeeee eeeeeeeee eee eee eeeee eee ee eeeeee eeeeeeeee ee e eeeeee ee eeeee.
M eeee ee 8-{8-[8-(eeeeeeeee)eeeeee]eeeee}-8-eeeeeeeeeeee (888; 8.8 e, 88.8 eeee) ee MeMM (888 eM) eee eeeeee ee −88 °M eee eeeeeee eeee M8 eeeee MMM eeeeee eee eeeeeeeeeeeee ee eeeeeeee eeeeeeee (eeeee 88 eee). Mee eeeeeee eee eeeeee eeee M8 eee 88 eee ee −88 °M eee Me8M (88.8 eM) eee eeeee ee eeee eeeeeeeeeee. Mee eee eee eeee eee eeeeeee eee eee eeee eee eeeeeee ee ee eee 88 e. Mee eeeeeee eee eeeeeeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8 eeee 88:8) ee eeeeee 8-[8-(eeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeeeeee[e]eeeee-8-ee (888) ee e eeeeeee eeeee eeeeee eee (8:8 eeeeeee ee eeeeeeeeeeeee); eeeee: 8.88 e (88%).
Me e eeee ee 8-[8-(eeeeeeeee)eeeeee]-8-eeeeee-8,8-eeeeeeeeeeee[e]eeeee-8-ee (888; 888 ee, 8.88 eeee) ee eeeeeee (88 eM) (MMMMMMM: eeeeeeeeee) eee eeeee MeMM (88.8 ee, 8.88 eeee). Mee eeeeeee eee eeeeeeee eee 8 e eeeee e Meeeeee eeeeeeeee eeeeeeeeee 8-Å eeeeeeeee eeeeee. Meeee eeee eeee eee eeeeeee eee eeeeee, eeeeee eeee eee. MeMMM8 (8 × 88 eM), eee eeeee (MeMM8). Mee eeeeeee eee eeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeee/MeMMe 88:8) ee eeeeee eee eeeeeee ee e eeeee, eeeeeeeee eee; eeeee: 888 ee (88%).
Meeee Meeee[e]eeeee-8-eeeeeeeeeeee 888; Meeeeee Meeeeeeee:[888]
MMMMMMM: Meeeeeeeeeeeeeee eeee ee eeeeeeeee eeeeeeeeeee ee eee eeee, eeee, eee eeeeeeeeeee eeeee.
Me e eeeeeee eeee ee e eeeeeeeeeee 8-eeeeeeeeeeeeeeeeeee 888 (8 eeee) ee MM8Me8 (88 eM), eee eeeee eeeeeeee MMM8 ee Me8M (8.88 eM, 8.8 eeee). M eeee ee eeeee eeeeeeeeeeee (8.8 eM, 88 eeee) ee MM8Me8 (88 eM) eee eeee eeeee eeeeeeee, eee eeeeeeee eee eeeeeeeee eeeee M8 eee ee eeeeee eeeeeee eee eeee eee ee eeeeeeeeee 88–88 eee. Mee eeeeeee eee eeeeeeeeeeee eee eeeee M8MM8 (8.8 eM) eee eeeee eeee eeeeeeee. Meeee 88 eee, eee eeeeeee eee eeeeeee eeee MM8Me8 (88 eM) eee eeeeeeeeeee eeee eeeee MeMMM8. Mee eeeeeeeeeee eee eeeeeeee eee eee eeeeee eeee e eeeeeee ee eeeeeeeee eeeee eee Me8M (8:8). Mee eeeeeeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee eeeee (eeeeee eee, eeeeeeeee eeeee/Me8M 8:8 eeee 88:8). Meeeeeeeeee ee eee eeeeee eeee eee eeeeeee.
8-Meeee-8-(eeeeeeeeeeeeeee)eeeee[e]eeeee (888); Meeeeee Meeeeeeee:[888]
M eeee ee eeeeeeeeeeeeeeeeeee eeeeeeeeeeeee (88 ee, 8.88 eeee, 8.8 eeeee) eee MeMM8 (88 ee, 8.88 eeee, 8.8 eeeee) ee e eeeeeee ee MM8Me8 eee M8M (8:8.8; 8.8 eM) eee eeeeeee eee 8 e ee e eeeeee Meeeeee eeee (88 eM) ee ee eee eeee eeeee eeeee. Mee eeeeee eeeeeee eee eeee eeeeee ee −88 °M ee e eee-eee/eeeeeee eeee eee eeeeeee eee 88 eee, eeeeeeee ee eee eeeeeeee ee 8-eeeee-8-eeeeeeeeeeeeeeeeeee (88 ee, 8.88 eeee) eee MM8•MMe8 (88 μM, 8.88 eeee, 8.8 eeeee). Mee eeeeeee eee eeee eeeeeee ee eeee eeeeeeeeeee eeeee MMM eeeeeeee eeeeeeeee eeeeeeeeee. Mee eeeeeeee eee eeeeeeee ee eee eeeeeeee ee MeMM (8 eM) eeeeeeee ee eee. MeMMM8, eee eee eeeeeee eee eeeeeeeee eeee MM8Me8 (8 ×), eeeee (MeMM8), eee eeeeeeeeeeee. Mee eeeee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MM8Me8) ee eeeeee eee eeee (8M*,8M*)-8-eeeee-8-(eeeeeeeeeeeeeee)-8,8-eeeeeeeeeeee[e]eeeee-8-ee (888) ee e eeeee; eeeee: 88 ee (88%).
(8M*,8M*)-8-Meeee-8-(eeeeeeeeeeeeeee)-8,8-eeeeeeeeeeee[e]eeeee-8-ee (888; 888 ee, 8.888 eeee) eee eeeeeeeee ee eeeeeee (88 eM) eee MeMM (888 ee, 8 eeee) eee eeeee. Mee eeeeeee eee eeeeeeee eee 88 e eeee e Meee–Meeee eeee. Mee eeeeeee eee eeeeee eee eee eeeeeee eee eeeeeeeeee. Meeeeeeeee eeeeeee e eeeee eeee ee eeeeee eee (eeeeeee) eeeeeeee eee eeeeeee ee e eeeee eee; eeeee: 888 ee (88%).
8-Meeeeeeeeee[e]eeeee-8-eeeeeeeeeeee (888):[888]
Me e eeee ee MMM (8 e) ee MMMe8 (88 eM) eee eeeee eeeeeeee MMMe8 (8.8 e) ee 8 °M. Meeee eee eeeeeee eee eeee eeeeeee ee 8–8 °M eee 8 eee, e eeee ee eeeee[e]eeeee-8(8M)-eee (88; 8.8 e, 8.88 eeee) ee MMMe8 (8.8 eM) eee eeeee eeeeeeee eeeee eee eeeeeee eee eeee eeeeeeee eee 88 e. MMMe8 eee eeeeeee eeeee eeeeeee eeeeeeee eee M8M eee eeeee ee eee eeeeeee. MMMe eee eeeee eeeee eM 8, eee eeee 8 M ee MeMM eee eeeee eeeee eM 8 eee eeeeeee. Mee eeeeeee eee eeeeeeeee eeee MM8Me8 eee eeeee (Me8MM8), eee eee eeeeeee eee eeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeeee (eeeeee eee, MMMe8) ee eeee eee eeeeeee ee e eeee eeeeee eeeee; eeeee: 888 ee (88%); ee 88 °M.
Meeee[e]eeeee-8-ee (888); Meeeeee Meeeeeeee:[888]
Me e eeee ee 8-eeeeeeeeeeee[e]eeeee-8(8M)-eee (888; 8.88 e, 88.8 eeee) ee MMM (888 eM) ee ee eee eeeee Me8M (8.88 e, 88.8 eeee) eee MMMMMMe (88.88 e, 88.8 eeee). Meeee eee eeeeeee eee eeee eeeeeee eee 8 e, eee eeee eee eeeeeee eeee Me8M (888 eM) eee eeeeee eeee eee. ee MM8Me (888 eM) eee eeeee (888 eM). Mee eeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee ee eeee eee eeeee eeeee ee 888 ee e eeeeee eee, eeeee eee eee eeeeeee eeeeeeee. M eeee ee eeee eeeee eeeee (88.8 e, 888 eeee) ee MeMM (888 eM) eee eeeeeee eeee MeMM8 (8.8 e, 888 eeee) ee eeee eeeee eeeeeeee ee ee eeeee MMM eeeeee eeeeeeeeee ee eee eeeeeeee (ee. 8 e). Mee eeeeeee eee eeeeeeee eeee eeeeeee (88 eM) eee eeee eeeeeee eeee 8 M ee MMe (888 eM) eee eeeeeee ee eeeee ee ee eeeee eee eeeeeeee eee eeeeeeee (MMM, ee. 88 e). Mee eeeeeeeee eeee eee eeeeeeeeeeee ee 888 eM eee eeeeeeeee eeee MeMMe (8 × 888 eM). Mee eeeeeeee eeeeeeee eeee eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeeee 8:8), eeeeeeeee eee eeeeeee ee ee eee; eeeee: 8.88 e (88%).
8-(Meeeeeeeeeee)-8-eeeeeeeeeeee[e]eeeee (888):[888]
Me e eeee ee 8-eeeeeeeeeeee[e]eeeee-8(8M)-eee (888; 8.88 e, 88.8 eeee) eee eeeeeeeeeeeeeeeeee (88.8 eM) ee MMM (888 eM) eee eeeee e 8.8 M eeee ee MeMe ee eeeeee (88 eM, 888 eeee) ee −88 °M, eee eee eeeeeee eee eeeeeee ee −88 °M eee 8 e. MeMM (8.8 eM) eee eeeee eee eee eeeeeee eee eeeeeeeeee. Me eee eeeeeeeee eee eee eeeee eeeeeee (888 eM) eee MeMM•M8M (88 ee) eee eee eeeeeee eee eeeeeee ee 88 °M eee 8 e. Mee eeeeeee eee eeeeee eeee eee. MeMMM8 eee eeeee, eeeee (Me8MM8), eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, MeMMe/eeeeee 8:8 eeee 8:8) ee eeeeee eee eeeeeee ee eeeeeeeee eeeeee; eeeee: 8.88 e (88%); ee 88–88 °M.
References
| [381] | Meeeeeeeee, M. M.; Meee, M. M.; M’Meeee, M. M.; Meeeeeeee, M. M.; Meee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeee, M.; Meeee, M. M.; Meeeeeeeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M.; Meeeee, M. M., MMM; Meeeeee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M.; Meeeeeee, M. M.; Meeeee, M. M.; Meeeeeeee, M. M.; Meee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [382] | Meeeeee, M.; eee Meeeeeeeeee, M.; Meeee, M. M.; eee Meeee-eee Meeeee, M.; Meee, M. Me. M.; MMeeeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [383] | Meeeee, M. M.; Meeeee, M. M.; Meee, M. M., Mee. Meee., (8888) 8, 8888. |
| [384] | Mee’eee’ee, M. M.; Meee’ee, M. M.; Meeeeeee, M. M.; Meeeeeee, M. M.; Meeeeeeee, M. M., Meee. M. Mee. Meee. (Meee. Meeeee.), (8888) 88, 888. |
| [385] | Meeeeee, M.; Meeeeeee, M. M., Mee. Meee., (8888) 88, 8888. |
| [386] | Meeeeee, M. M., M. Meeeeeeeee. Meee., (8888) 88, 888. |
| [387] | Meeee, M.; Meeeeee, M., M. Mee. Meee., (8888) 88, 8888. |
| [388] | Meeeeee, M. M.; Meeeeeee, M. M.; Meeee, M. M.; Meeeeeeeee, M. M.; MeMeee, M. M.; Meeee, M. M.; Meeeeee, M. M.; Meeeeeeee-Meeeeee, M.; Meeeeee, M. M.; Meeeeee, M. M.; Meeeee, M. M.; Mee, M.-M.; Meeeeee, M.; Meeeee, M.; Meeeeeeeeee, M.; Meeeeeeeeeeeeee, M.; Meeee, M. M.; Meeeeeeeee, M. M.; Meeee, M. M.; Meeeee, M. M., M. Mee. Meee., (8888) 88, 8888. |
| [389] | Meeee, M. M.; Meee, M. M.; Meeeeeeee, M. M.; Meeeeee, M. M., Meeeeeeeeee Meee., (8888) 88, 8888. |
| [390] | Meeeee, M.; Mee, M.; Meeeeeeeee, M. M.; Meeeeeeee, M. M., Meeeeeeee M. Mee. Meee., (8888) 8, 8888. |
| [391] | Meee, M.; Meeeeeee, M.; Meeee, M.; Meeeee, M.; Meeeee, M.; Meeeee, M., M. Mee. Meee., (8888) 88, 8888. |
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