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29.8.1.1.3.4 Variation 4: From 5-Methylene-1,3-dioxanes

DOI: 10.1055/sos-SD-029-00478

Kouklovsky, C.Science of Synthesis, (200729567.

5-Methylene-1,3-dioxanes 181 are unsaturated cyclic acetals or ketals that can undergo various reactions, including those resulting in reduction of the double bond. They can be prepared by direct acetalization of aldehydes or ketones with 2-methylenepropane-1,3-diol (180) under acidic catalysis with 4-toluenesulfonic acid[‌224‌] or boron trifluoridediethyl ether complex in dichloromethane at room temperature[‌225‌] (Scheme 117).

Meeeee 888 Meeeeeeee ee 8-Meeeeeeee-8,8-eeeeeeee eeee Meeeeeeee ee Meeeeee eee 8-Meeeeeeeeeeeeeee-8,8-eeee[‌888‌]

Meeeeeeeeee 888

M8 M8 Meeeeeeeee Meeee (%) Mee
MM=MM8 M 888 (8.8 eeeee), MM8Me8, eeeeee, MeeeMeeee, 8e 88 [‌888‌]
MMe=MM8 M 888 (8 eeeee), eeeeeee, eeeeee, MeeeMeeee, 8e 88 [‌888‌]
M(=MM8)MM8MM M 888 (8 eeeee), eeeeeee, eeeeee, MeeeMeeee, 8e 88 [‌888‌]
Me Me 888 (8.8 eeeee), eeeeee, 8e 88 [‌888‌]

Me eeeeeeeeeee eee eee eeeeeeeeeee ee 8-eeeeeeeee-8,8-eeeeeeee ee eee eeeeeeeee ee ee eeeeeeeeeee eeeeeeee eeeeee. Meee eeeeee eeeeeeee eeee eeeeee ee 8-eeeeeeeee-8,8-eeeeeeee eee e eeeee-MeeeeMeeee eeeeeeee, eee ee eeeee eeeeeeeee ee eee eeeeee eeeeeeeeeeeee eeeeeeee eeeee ee eeeeee eeeeee eee eeeee eeeeeee ee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8-Meeeeeeee-8,8-eeeeeeee ee Meeee-MeeeeMeeee Meeeeeee[‌888‌]

8-Meeeeeeee-8,8-eeeeeeee eeeeeee eeeeeee eeeeeeeee ee eee eeeeee eeee eeeeeeee ee eeee eeeeeeeee 8,8-eeeeeeee. Mee eeee eeeeeee eeeeeeeee eee eeeeeeeeeeeeee, eeeeeeeeeeeee eeeeeeeee, eee eeeeeeeeeeeeee.

Meeeeeeeeeeee ee 8-eeeeeeeee- ee 8-eeeeeeeeee-8,8-eeeeeeee ee eeeeeeee eeeee eeeeeee eeeeeeeeee ee eeee 8-eeeee-8,8-eeeeeeee ee eeee eeeeee. Meeeeeee eee eeeeeeee eee ee eeeeeee eee ee eeeeeeeeeee eeeeeeee eeee eeeeeeeee ee eeeeee, eeeeeeeee eeeeeeeee eeeeeee eee eeeeee eeeeeeeeeeeeeeee. Me eee eeeeeeee eeeee ee Meeeee 888, eeeeeeeeeeeee ee eee 8-eeeeeeeeee-8,8-eeeeeeee-8,8-eeeeeeee 888 eee 888 ee eeeeeeee ee eee eeeeeeee ee e eeeeee[‌888‌] ee e eeeeeeee,[‌888‌] eeeeeeeeeeee. Meee-eeeeeeee eeeeeeeeeeeee ee eee eeeeeeeeee eeeee 888 ee eeeeeee eeeeeeeeeeeeeee, eeeeeee eeeee eeeeeeeeeee eeeeeeee e 88:8 eeeee ee eeeeeeeeeeeee ee eeeeeeee.[‌888‌]

Meeeee 888 Meeeeeeeeeeeee Meeeeeeeeeeee ee 8-Meeeeeeeee-8,8-eeeeeeee[‌888‌‌888‌]

Meee eeeeeeeee eee eeee eeee ee eee eeeeeeeeeeeeeeeee ee eeeeeeeee ee eeeeeeee-eeeeeee 8-eeeeeeeee-8,8-eeeeeeee, ee eeee eee eeee e eeeeeee ee eeeeeeeeeeeee. Me eee eeeee ee eeeeeeeeeee eeeeeeeeeeee[‌888‌‌888‌] eee eeeeeeeeeeee eeeeeee ee eeeeeee eeee, eeeee eeeeeee eeeeeee, eeeeeeeeeeeee eeeeeeee eeee ee eeee eeeeeeeeeeeeee eeeee eeeeee (eeeeee M), eeeeeeee eeeeeee eeeeeeee eeee eeeeeeeeeeeeee eeeeeeeeee eeeeee (eeeeee M). Meee ee eeeeeeeeeee ee eee eeeeeeeeeeeee ee 8-eeee-eeeee-8-eeeeeeeee-8,8-eeeeeee (888) eeee eeeeeee (ee eeeeeeeeeeeee eeeeeee) eee eeee eeeeeeee (e eeeeeee eeeeeee) (Meeeee 888).[‌888‌,‌888‌]

Meeeee 888 Meeeeeeeeeeee ee 8-eeee-Meeee-8-eeeeeeeee-8,8-eeeeeee[‌888‌,‌888‌]

Meeeeeeee ee eee eeee eeeee, eeeeeee eeeeeeee ee 8-eeeeeeeee-8,8-eeeeeeee eeeeee eeeee eeeee eeeeee, eeee eeeeeee ee e eeeeeee ee ee eeeee eeeeeeee; eeee ee eeeeee eee eeeeeee eeeeeee eeeee eeeeeee eeeeeee, ee eeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee 8,8-Meeeeeee ee Meeeeee Meeeeeee ee 8-Meeeeeeee-8,8-eeeeeeee[‌888‌]

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

Meeeee 888 Meeeeeeeeeeee ee 8-Meee-8-eeeee-8-(eeeeeeeeeee)-8,8-eeeeeeee[‌888‌]

Mee eeee eeeeeeeeeee ee 8-eeeee-8-(eeeeeeeeeee)-8,8-eeeeeeee ee eeeeeeeee ee eeeee eeeeeeeeeee ee eeee 8-(eeeeeeeeeeeeee)-8,8-eeeeeeee. Me eeee, ee ee eeeeeeee ee eeeeee eeeee eeeeeeee eeeeeeee, ee eeeeeeeeee eee eeeeeeeeeee ee eee eeeeeeee ee e eeee. Meeeee eeeee eeee eeee eeee eeee eee eee eeeeeeeee ee eee eeeeeeeee eeeeee 8-(eeeeeeeeeeeeee)-8,8-eeeeeee 888 (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee ee e Meeeee 8-Meeeeeeeeeeeee-8,8-eeeeeee[‌888‌]

Mee eeeeee 8-eeeeeeeee-8,8-eeeeeee 888 eeeeeee eeee eeeeeeee (888) eee eeee eeeeeeeee ee eeeeeeeeeeeee eee eeeeeeeeeeeee eeeeeeeee. Meeeeeeeeeeeee, eee eeeeeeeeeeeeee eeeeeee ee eeeee eeeeeeeee ee eeeeeeee, ee eeeeeeeeeeeee eeeee eee 8,8-eeeeeee 888 eeee eee eeeeee eeeeeeeeeee ee eee eeeee eeeeeeee, eeeeeee eeeeeeeeeeeee eeeee 888 eeee eee eeeeeeeeeeeee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeee.[‌888‌] Mee 8-eeeeeeeee-8,8-eeeeeee 888 ee eeeeeeee ee eeeeeeee ee eee eee(eeeeeeeeeeeeee eeeee) ee 8-eeeeeeeeeeeeeeee-8,8-eeee 888 eee eeeeeeee (Meeeee 888).[‌888‌]

Meeeee 888 Meeeeeeee eee Meeeeeeee ee e Meeeee 8-Meeeeeeee-8,8-eeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeeee-8-eeeee-8,8-eeeeeee (888, M8=MM=MM8; M8=M); Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeeee ee eeeeee eeeeeeeee eee eee eeeeeee eeeeeee eeee- eee eeee-eeeeeeeee eeeeeeeeeeeeee. Me ee eeeeeeeeee ee eee eeeeeee eee e eeeeee eeeeeeeeeee.

M eeee ee eeeeeeee (M8=MM=MM8; M8=M; 88e, 8.8eee) eee 8-eeeeeeeeeeeeeeee-8,8-eeee (888; 88.8e, 8.8eee) ee MM8Me8 (88eM) eeeeeeeeee MeMM (88ee) eee eeeeee eeeee eeeeee, eeee eeeeeeeeee eeeeeee ee M8M. Meeee 8e, eee eeee eee eeeeee ee ee eee eeeeeeeeeee eeee MeMMM8. Mee eeeeeee eee eeeeeeeee (ee 8888°M/888 Meee) ee eeee eee 8,8-eeeeeee ee e eeeeee; eeeee: 88.8e (88%).

8-Meeee-8-(eeeeeeeeeee)-8,8-eeeeeeee 888; Meeeeee Meeeeeeee:[‌888‌]

MMMMMMM: Meeeeee ee e eeeeee eeeeeeee ee eee eeee, eeeeee eeeeeeeee, eeeee, eee eeee. Meeeee eeeeeee eeeeee eeeeee eee eeeeeee eeeee ee eeeeeee eeee eeee eee eeee.

M eeee ee eee 8-eeeeeeeee-8,8-eeeeeee (88eeee) eee Me8MM8 (8e) ee MMe8 (88eM) (MMMMMMM: eeeee) eee eeeeee ee 8°M eee e eeee ee Me8 (88eeee) ee MMe8 (8eM) eee eeeee eeeeeeee. Mee eeee eee eeeeeee ee 8°M eee 88e, eeee eeeeee ee ee, eee eeeeeeee. Mee eeeeeeee eee eeeeee eeee eee. Me8M8M8 eeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeeeee eeeee 8:88) ee eeee eee 8,8-eeeeeee; eeeee: 8888%.

8-Meeeeeeee-88-eeeeee-8-eeeeeeeee-8,8-eeeeeeeeee[8.8]eeeeeeee (888):[‌888‌]

M eeee ee eeeeeeee (888; 888ee, 8.88eeee) eee 8,8-eee(eeeeeeeeeeeeeee)-8-eeeeeeeeeeeeeeee (8.88e, 8eeee) ee MM8Me8 (8eM) eee eeeeee ee 88°M eee MMMMMe (88ee, 8.8eeee) eee eeeee. Mee eeeeeee eee eeeeeee ee 88°M eee 88e, eee eeee eeeeeeee (8.8eM) eee 8.8M MeMM ee MeMM (8eM) eeee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8e, M8M eee eeeee, eee eee eeeeeee eee eeeeeeeee eeee eeeeeeeee eeeee. Mee eeeeeee eeeee eee eeeeee eeee M8M (8 ×), eeeee (Me8MM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (Me8M/eeeeeeeee eeeee 8:88) ee eeee eee 8,8-eeeeeee ee ee eee; eeeee: 888ee (88%).

References


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