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29.8.1.2.1.1 Variation 1: Cleavage To Give Carbonyl Compounds and 1,3-Diols

DOI: 10.1055/sos-SD-029-00478

Kouklovsky, C.Science of Synthesis, (200729576.

Like other acetals, 1,3-dioxanes are stable under basic conditions. Hydrolysis of 1,3-dioxanes occurs, therefore, under acidic catalysis. Methods for hydrolytic cleavage of 1,3-dioxanes are similar to those used for the deprotection of 1,3-dioxolanes (Scheme 133).

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Meeeeeeeee eeeeeeee ee eeeeeeeee eeeeeeeee eeeee eeeeeee eeeeee eeeeeeeeee. Meeeeeeee eee eeee (eeeeeeeee ee eeeeeee) eee ee eeee, eeeeeeee eeeeeeeeeeee eeee, eeeeeeee eeee, eeeeee eeee, eeeeeeeeeeeeeee eeee, eee 8-eeeeeeeeeeeeeee eeee eee eeeeeeee eeeeeeee. M eeeeeee eeeeeeeeeeee eeeeeeeee eeeeeeeee eeeeeeee eeeeeeeee ee eee 8,8-eeeeeee eeee ee eeee ee e eeeee/eeeeeee eeeeeee eeeeee. Meeeeee, 8,8-eeeeeee, ee eeeeeeeeeeeeeee eee eeeeeeee eeee ee eeeeeeeeee. Meeeeeeeeeeeeee eee eeee ee eeee. Meeee eeeeeeeeeeeeee eee eeeeeee ee eee eeeeeeeee, eee eeeeeeee eeeeeeee eee/ee eee 8,8-eeee eee eeeeeeeee. Meeeeeeeeeeee eeee eeeee eee eeee ee e eeeeeeeeee eeeeeeeee, ee eeeeeeeeeee ee eee eeeeeeeeee ee eee 8,8-eeeeeee 888 ee eee eeeeeeeee ee eeeeeeeeeee eee 8,8-eeee 888 (eeee eeee eee eeee-eeeeeeeeeeeeeeeeee eeeee ee eeeeeeeee) (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeee ee e 8,8-Meeeeee eeee ee Meeeee Meeeeeeeeeeeeee Meeeeeee[‌888‌]

Mee eeeeeee eeeee eee eeeeeeeeee ee eeeeee eeeeeee eee ee eeeeeee: eeeeee-eeeeeee 8,8-eeeeeeee eee eeeeeeeeee eeeeee eeee eeeeeeee-eeeeeee 8,8-eeeeeeee; eeeeee-eeeeeee 8,8-eeeeeeee eee eeeeeeeeee eeeeee eeee eeeeee-eeeeeee 8,8-eeeeeeeeee; eeeeeeee-eeeeeee 8,8-eeeeeeeeee eee eeeeeeeeee eeeeee eeee eeeeeeee-eeeeeee 8,8-eeeeeeee. Meeeeee, eeeee eeeeeeeeee eeee ee ee eeeee eeee eeeeeeeeeeeee, eeee ee eee eeeeeeee ee eee eeeeee ee ee eeeeeee eeeee. Mee eeeeeeee, ee ee eeeeeeee ee eeeeeeeeeee eeeeeeeee e eeeeeeee 8,8-eeeeeeeee ee eee eeeeeeee ee ee eeeeeeee 8,8-eeeeeee ee eeeeeeeee ee eee eeeeeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee Meeeeeeeeeee ee e 8,8-Meeeeeeee ee eee Meeeeeee ee e 8,8-Meeeeee[‌888‌]

Mee eeee ee eeeeeeeeee ee eee 8,8-eeeeeee eeee eeeeeee ee eee eeeeeeeeeeee ee eee 8,8-eeee eeeeeeee. Meeeeee eeeeeee ee eee eeeeeeeeee ee eeeeee eeeeee eeeeeee eeee eeeeeeee eeee eeeeeeeeeeee ee eee 8-eeeeeeee eeeeeeee eeeeeeeeeee eee eeeeee eeeeee eeeeeeeeee (Meeee 8).[‌888‌]

Meeee 8 Meeeeeee Meeee eee eee Meeeeeeeee ee Meeeeee Meeeee Meeeee Meeeeee[‌888‌]

8,8-Meeeeee Meeeeeee Meeee Mee
8 [‌888‌]
88.8 [‌888‌]
8 [‌888‌]
8.888 [‌888‌]
8.888 [‌888‌]
88 [‌888‌]
888 [‌888‌]
88.8 [‌888‌]
8.88 [‌888‌]
8.88 [‌888‌]

e Meeeeeeeee: 8.888M MMe ee eeeeeee/M8M (8:8), 88°M.

Meee, 8,8-eeeeeeee-8,8-eeeeeeee eee eeeee eeeeee eeeeee eeeeee eeeeeeeeee eee eee eeeeeeeee ee eeeeeeee eeeeee eee eeeeeee ee eeeee eeeeeeeeee eeeeee. M eeeeeeee eeeeeee ee eeeeeeee ee e eeeeeeeee ee ()-eeeeeeeeee, eeeee e eeee-eeeeeeeeeeeeeeeeee eeeee ee eeeeeee eeee eeeeeeeeee 8-eeeeeeeeeeeeeeee ee 88°M ee eee eeeeeeee ee e eeeeeeeeeee 8,8-eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee Meeeeee ee e Meeee Meeeeeeeee Meeee ee eee Meeeeeee ee e 8,8-Meeeeeeeeeeee 8,8-Meeeeee[‌888‌]

Mee eeeeeeee eeeeeeeeeeeee ee 8,8-eeeee eee eeee eeee ee eeeeeeeee ee eee eeee ee eeeeeeeeee. Me eee eeeeeeeeee eeee eee eeeeeeeeee ee eeee-8,8-eeeee eeeeeeeee eeee eeeeee eeee eeeee eee-eeeeeee.[‌888‌] Meee, eeeee eeeeeeeeee eeeeeeeeee ee ee eeeeeeee ee eeeeeeeee eeee eee eeeeee; eeee eeeeeeeee ee eeeeeeeee eeeeee eee eee eeeeeeeeee ee eeeeeee ee 8,8-eeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeeee ee eee eee- eee eeee-Meeeeeeeeeeee ee e 8,8-Meee ee Meeeeeeeee ee eee Meeeeeeeee[‌888‌]

Me eee eee eeeeeeeeeeeee eeeeeeee, eeeeeeeeee ee eeeeeee eee ee eeeeeeeee eeee eeeee-eeeeeeeee eeeeeeee. Meeeee eeee ee eeee(MMM) eeeeeeee eeeeeeee eeee eeeeee eee eee eeeeee eeeeeeee eee eeee eeeeeeeeeeeeee eeeee eeee eeeeeeeeee. Meeeee eeeee eee eeee ee eeeeeeee eeee Meeee eeeee ee eeeeeeeeeeeee eeeeeeee. Meeeeee eeeeeeee eeee eeee eeee, eeeeeeeee eeeeeeeeeeeeeeeeeee, eee(eeeeeeeeeeee)eeeeeeeeeeeeeeeee(MM), eeeeeeee(MMM) eeeeeeee, eee eeeeee(MMM) eeeeeeee. Meee ee eeeee eeeeeeee eeeeeeeeeee eeeeee eeeeee-eeeeeee eeeeeee ee eee eeeeeeee ee eeeeeeee-eeeeeee eeeeeee.

Meeeeeeeeeeeeeeeee eeeeeeeeee eeeee eee eeeeeeeeeeee ee eeeeeee eeeee eeee eeee eeeeeeeeee eee eeee eeee eeeeeee ee eee eeeeeeeee ee eeeeee-eeeeeeeeee eeeeeee eeeeeeee. Meeeeeeee ee 8,8-eeeeeeee eeee e eeeeeeeee eeeeee ee ee eeee ee eeeeeeee eeeeee eee eeee eeeeeeeeeeee ee eeeeeeeeee eee eeeeeee eeeeeee. M eeeeeeeeeeeeee eeeeeee ee ee eee eeeee eeee ee eee eeeeeeeee ee eeeeeeeee (888) eeee eeeeeeeeee 888, eeeee eeeee eeeeeeeeeeeeee eeeeeee eee e eeee-eeeeeeeeeeeeeeeeeee eeeee eee eeeeeee eeeeeeeeeeeee (Meeeee 888).[‌88‌]

Meeeee 888 Meeeeeee ee 8,8-Meeeeeee ee Meeeeeeeeeeeeeeeee ee eee Meeeeeeee ee Meeeeeeee[‌88‌]

Meeeeeeeeeee (ee 8-eeeeeeeeeeeeeeeeeee) eeeeeee eee ee eeeeeee eeeee eeee eeeeeeeeee ee eeeeee eeeeeeeee eeeeeeeeeeeee, eeeeeeee eeee eee eeee eeeeeeee eeee eeeeeee ee eeeeee eeeeee eeeeee. Meeee eee-eeeeeeee eeeeeee eee eeee eeeeeeeee eeeee eeeee eeeeeeeeee. Meeeeeeee(MM) eeeeeeeee (Meeeeeee'e eeeeeeee) ee eee eeee eeeeeeeee eeeeeeee eee eeee eeeeeeee, eee ee eeee ee eee eeeeeeeee ee 8,8-eeee 888 eeee 8,8-eeeeeee 888. Meee eeeeeeeee ee eeeeee eee eeeeeeee ee eeeeee, ee ee ee eeeeeeee ee eeeeeeeeeee eeeeeeeeeee ee eeeeee ee eee eeeeeeee ee eee eeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Meeee ee Meeeeeeeeeeeee ee 8-Meee-8,8-eeeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8M,88M)-88-[(8M,8M,8M,8M)-8,8-Meeeeeeee-8,8-eeeeeeeeeee-8-eeee]-8,8-eeeeeeee-8-(eeee-eeeeeeeeeeeeeeeeeee)eeeeeeeeeeeee-8-ee-8-eee (888):[‌888‌]

M eeeeeee ee MM8Me8 (88eM), M8M (8eM), eee MMM (8eM) eee eeeeee eeeeeeeeee eee eeeeeeeee. Meee ee eee eeeeeee eeeee (8eM) eee eeeee ee eee eeeeeeeeeeee 888 (88.8ee, 8.888eeee) eee eee eeee eee eeeeeee ee ee eee 8e. Me eee eeee eeeeeee eeee MM8Me8, eeeeee eeee eee. MeMMM8 eeee (88eM) eee eeeee (88eM), eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) ee eeee eee eeee ee e eeeeee eee; eeeee: 8.8ee (88%).

()-Meeeeeeee (888):[‌88‌]

Me e eeee ee eee eeeeeeeee 888 (8.8ee, 8.8888eeee) ee MeMM (8eM) eee eeeee MMMM (8 eeeeeee) eee eee eeee eee eeeeeee ee ee eee 88e. Mee eeeeeee eee eeeeeee eeee MeMMe (8eM) eee M8M (8eM). Mee eeeeeee eeeee eee eeeeeeeee eeee MeMMe (8 × 8eM) eee eee eeeeeeee eeeeeee eeeeee eeee eeeeee eeee eeeee (8eM) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeee MMMM (e-88 Meeeee, MeMM/M8M 8:8) ee eeee eee eeeeeee ee e eeee eeeee; eeeee: 8.8ee (88%).

(8M,8M,8M,8M,8M)-8,8,8-Meeeeeeee-8-(eeeeeeeeeeeeeeeeee)eeeeee-8,8-eeee (888):[‌888‌]

Me(MM)8 (8.888e) eee eeeee ee e eeee ee eee eeeeee 888 (8.888e, 8.8eeee) ee eMeMM (8eM) eee M8 eee eeeeeee eeee eee eeee eee 88eee. Mee eeeeeee eee eeeeeee eee 88e eeeee M8 (888Meee), eeee eeeeee eee 88eee eeee M8, eee eeeeeeee eeeeeee e eee ee Meeeee. Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (MeMMe/eeeeeee 8:8 ee 8:8); eeeee: 8.888e (88%).

References


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