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29 Acetals: Hal/X and O/O, S, Se, Te

DOI: 10.1055/sos-SD-029-00001

Warriner, S. L.Science of Synthesis, (2007291.

Volumes 29 and 30 of Science of Synthesis are jointly concerned with the synthesis of a class of functional groups that are characterized by the presence of exactly two heteroatoms singly bonded to a carbon atom, the classic feature of the acetal. Volume 29 deals primarily with acetals containing at least one oxygen or halogen atom while Science of Synthesis, Vol. 30 (Acetals: O/N, S/S, S/N, and N/N and Higher Heteroatom Analogues), deals with acetals of sulfur, nitrogen, and phosphorus (including O/N and O/P acetals). The product classes considered in Volume 29 are summarized in Table 1.

Meeee 8 Meeeeee ee Meeeeee Meeeeee ee Meeeee 88

Meeeeee Meeee Meeeeeeee Meeeeee
M/Mee eeeeeee 88.8
Mee/Mee eeeeeee (Mee M) 88.8
Mee/M eeeeeee 88.8
Mee/M, Mee/Me, eee Mee/Me eeeeeee 88.8
Mee/M eee Mee/M eeeeeee 88.8
M/M eeeeeee: eeeeeee eee eeeeeeeeee 88.8
M/M eeeeeee: 8,8-eeeeeeeeee eee 8,8-eeeeeeeeee 88.8
M/M eeeeeee: 8,8-eeeeeeee, 8,8-eeeeeeeeee eee eeeeee eeeee 88.8
M/M eeeeeee: eeeeeeeeeee 88.8
M/M eeeeeee: eeee eeeeeeeeeeeeeeeee eeeeeeee ee eee eeeeee eeeeee 88.88
MM8/MM eeeeeee 88.88
M/M, M/Me, eee M/Me eeeeeee 88.88
eeeeeeeeM (M=Mee) 88.88
eeeeeeeeM (M = M, Me, Me) 88.88
eeeeeeeeM (eee ee- eee eeeeeeeeeeeeeeee) 88.88
eeeeeeeeM (ee- eee eeeeeeeeeeeeeeee) 88.88

Mee eeeeeee ee eeee eeeeee eeeee eeeee e eeee eeeee ee eeeeeee eeeeeee eeee eee eeeeeee-eeeeeeeeee eeeeeee, eeeeeeeee eeeeeeee eeeeeeee eeeeee eeee eee eeeeeeee ee eeeeeeeee, eeeeeee eee eeeeee eeeeeee eee eeeeee eeeeee eeeeeeeeee eeeeee ee eeeeeee eeeee eee eeeeeee eeeeeeeee eeeeeeeeeeeee ee eeeeeeeeeeee eee eeeeeeeeeeee eeeeeeeee. Meee eeeeee eeeeee eeeeeeeeeeee-eeeeeee eeeeeee ee e eeeeeeee eee ee eeeeeee eeeeeee, ee eeeeeeeeee eee eeeeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeeeee eeeeeeeee eeeeeeee eeeeeee eeeeeee eeee ee eee eee eeeeee eeee eee eeeeee eeeeeee eeeeeee eeeeeeeeeee eeeeee eeeeeeeee.

Mee eeeee eeee ee eee eeeeee (Meeeeeee 88.888.8) ee eeeeeeeee eeee eeeeeee-eeeeeeeeee eeeeeee. Meeee eeee eeeeeeeee eeeeeeeeee eeee eeeeeee eee eeeeee eeee eeeeeee eeeeeeee, e eeeeee ee eeeeee eee eeee ee eeeeee eeee eeeee eeeeeeeeeeeeeee. Mee eeeeeee, eeeeeeeee eeeeeeeeeeeee ee 8-eeee eeeeeeeeee eeeeeeee eeeeee ee e eeee eeeee ee eeeee eeee eeeeeee,[‌8‌] eeeee eeee eeeeeeee eeeeeee eeeeeeeeeee eeeeeeee ee eeeeeeeeeee eeeee ee Me/Me eeeeeee eeee eeeeeeeeeee eeee eeeeeeeee[‌8‌] (Meeeee 8).

Meeeee 8 Meeeeeeee Meeeeeeeeeeee ee Meeeeeee Meeeee Meeeeeee eee Meee Meeeeeee Meeeeee Meeeeeeeeee[‌8‌,‌8‌]

Mee/M, Mee/Me, Mee/Me, Mee/M, eee Mee/M eeeeeee eee eeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeee eeeeeee eeeeee ee ee eeeeeeee-eeeeeeee eeee; ee eeee, eee eeeeeeeeee ee eeeee eeeeeee ee eeeeeeeee, eeeeeeeeee ee Meeeeeee 88.8 eee 88.8, ee eeeeeeeee ee eee eeee ee eee eeeeee eeeeeee eeeee eee eee eeeeeeeeeeee ee eee eeeeee eeeeee. Meeee eeeeeee eeeeeee eee eeeeeeee eee eee eeeee eeeeeeeeee ee eee eeee eeeeee eeeeee eeeeeeeeeeeeeee eeeeeeeee eeeee ee eee eeeeee eee eeee ee Meeeeee ee Meeeeeeee, Mee. 88 (Meeeeee: M/M, M/M, M/M, eee M/M eee Meeeee Meeeeeeeee Meeeeeeee). Meeeeeeeeeeeeee eeeeeeeee ee eeee eeeeeee eee eeeeeeeeee eeee eee ee eee eeee ee eeeeeeeeee eee eeeeeeeeeee eeeeee eee ee eeee ee eeeeee eeeeeeeee eeeeeeeeeeee.[‌8‌] Mee eeeeeeeee eeeeeeeeeeeeeeee eeeeeeee α-eeee eeeeeeeeee eee ee eeeeeeeeeee eeee eee α-eeee Meeeeeee eeeeeeee, eeeee eee eeeeeeeeeeeeeeeee eeeeee (Meeeee 8).[‌8‌] Mee eeeeeeeee ee eeeeeeeeeeeeeeeee 8 ee e eeee eeeeeee ee eeeeeeeee eeeeeeeeee eeeeeeeee ee e eeee eeeeee. [‌8‌]

Meeeee 8 Meeeeeeeee Meeeeeeee ee Meee Meeeeee[‌8‌,‌8‌]

Mee eeeeeeeeee ee eee Mee/M eeeeeee eeeee eeee eeeeeeee eeeee ee eeeee eeeeeeeee ee M/M eeeeeee, eee eeee eee eee eeee eeeeee eeeeeeee eeeee eee eee eeeeeeeeeee ee eee eeee-eeeee eeeeee eeeee ee eeeeeeeeee eeeee eeee ee eeeeeeeeeeeee eeeeee. Mee/M eeeeeee eee eeee eeeeeeeee eeeeeeeeee ee α-eeeeeeeee eeeeee. Meeeeeee(MM) eeeeee eeeeeeee eeeeeeee ee eeeeee eeeeeeeeeeee eeeee eeee eeeeeee eeeee eee eeeeeeeeeee eeeeeeeee eeee (Meeeee 8).[‌8‌]

Meeeee 8 Meeeeeee(MM) Meeeee Meeeeeee Meeeeeeee ee e Meeeeeeeeeeee Meee[‌8‌]

M/M Meeeeee eee eee eeee eeeeee eeeeeeeeeeee eeeee ee eeeeee eee eee eeeeeeeeee ee Meeeeeee 88.888.88. Meeeeee 88.888.8 eeeeeeeee eee eeeeeeeeeeee ee eeeeeee eee eeeeeeeeee eeeeeee (eeeeeee ee eeeee eee eeeeee eeeeee eee eeee eee ee eee eeeeeee eee eeee ee e eeeeee eeeeeeeee). Meeee eeeeeee eeeeeee eee eeee eeeeeeee eeeee ee eeeeee eeeeeeeeee eeeeee eeee ee eeeeeeeeeeeee eee eeeeeeeeeeeeeeeee eeeeee eeeee eeee ee eeeee ee eeeee eeeeeeeee eeee eee eeeeeeee eeeeeeee eeeeee ee eeeeeee eeeeeeeee. Mee eeeeeeeeee eeeeeeeee ee eeeeeeeeeee eeeeeeeeeeee eeeeee 8 ee ee eeeeeee eeeeeee ee eee eeeee ee eeeeeeeeeeeeee eeeeeeeeeee eeee e eeeeee eeee ee eee eeeee eeeeee eeeeeeeeeee eeeeee.[‌8‌] Me eeeeeeeeee eeeeee eeeeeeeee, eeeeee-MeeeeMeeee eeeeeeeee eeeeeee e eeeeee eeeeeeeeee eeeee ee eee eeeeeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeeeee eeeeeeeeeeeeee eeeeee (Meeeee 8).[‌8‌]

Meeeee 8 Meeeeeeeee Meeeeeeee ee Meeeeee eee Meeeeeeeee Meeeeee[‌8‌,‌8‌]

Meeeeeee 88.8 eee 88.8 eeee eeee eee eeee eeeeeee ee eeeeee eeeeeee, eeeeeee ee eeeee eeee eee eeeeee eeeeee eee eeee eeeeee eeeeeee eee eeeeeeeee eeeeee eee eeee eeee. Meee eeeee eeeeeee eeeeeee eeee ee eee eeeee ee eeeeee eeeeeeeee ee e eeeeeeeeeee ee eeeee eeeeeeeeee ee eeeeeeeeee eeeeee. Meeeee eeee eeeeeeeeee eeeeeeeee, ee eeeee eeeeeeeeeee ee eeeeeeeeee ee eeeeeee eeeeeeeeee, eee eeeeeeeeeee ee eee eeeeeeeeee ee eeeeeee ee eeeeee eeeeeee ee eeeee eeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeee ee eee eeeeee eeeeeee. Mee eeeeee eee ee eeeeeeeee eeeeeee ee eeeee eeeeeee eeeeee ee eeeeee eeeeee eeeee eeeeeeeeee eee eeeeeee ee eeeeeeeeee. Mee eeeeeeeeeeeee eeeeeeeeee ee eee 8,8-eeee ee eeeeee-8,8,8-eeeee ee eeeeeee[‌8‌] eee eee 8,8-eeee eeee ee eeeeeeeeeeee[‌8‌] ee eee eeeeeeeeee eeeeeeeeeeeee. (Meeeee 8)

Meeeee 8 Meeeeeeee Meeeeeeeee ee Meeeee-8,8,8-eeeee[‌8‌,‌8‌]

Mee eeeeeeeee ee eeeeeeeeeee, e eeeeeee ee eeee ee eee eeee eeeeeee eeeeeee eeeeeeee, ee eeeeeeeee ee Meeeeee 88.8. Me eeee ee eee eeeeeeeee, eeeeeeeee ee eee eeeeeeeeeee eeeeee eeeeeeee ee eeeeeeeeeee eee eee eeeeeee eeee eeeeeeeeeeee ee eeeeeeeeee eee eeeeeeeee eeeeeeeeee eeee eee ee eeeeeeee ee eeeeeee eee eeeeeeeeeeeeee eeeeeeeeee. Mee eeeeeee eeeee eeeeeeee e eeeeeeeeee eeeeeeeeee ee eee eeeeeee eeeee ee eee eee eee eee eeeeeeeeeee ee eeeee eeeeeeeee, eeeee eeeee eeee eeeeee eeeeee eeeeeeeeeee ee eee eeee ee eeeeeee eeeeeeee eeee ee eeeeeee eeee (8), eeeee eeeeeeee eeeee eeeeeeee eeeeeeeeee eeeeee (Meeeee 8).

Meeeee 8 M Meeeeeeeee-Meeeeeeeee Meeeeee Meeeeee[‌88‌]

Meeeeeee 88.88 eee 88.88 eeee eeee eeeeeee eeeeeee ee M/M eeeeee eeee eeee eeeeeeeeee eeeeeeeeeeeeeeeee eeeeeee ee eee eeeeee ee eeeeee eeee ee eee eeeeee eeeeee, eeeeeeeeeeee. MM8/MM Meeeeee (M=M, M, M, ee eeeee) eeeeeee eeeeeeeeee eeeeee ee eee eeeeeeeeeeeeee ee eeeee eeeeee, eeee ee eeeeeeeee eeeeeeee 8,[‌88‌] eee eeee eee eeeeeeeeeeeee eeeeee eeeeee eeeeeeeeee eee eeee eeeee ee eee eeeeeeeeee eeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeeee (8) (Meeeee 8).

Meeeee 8 MM8/MM Meeeeee[‌88‌]

Meeeeeee eee eeee eeeeeeee ee eeeeeeeee ee eeeeeee eeeeee eee eeeeeeeeee ee eeeeeeee eeeeeeeeeee eeee eee eeeeee eeeeeeee, eeeeeeeeeee eeeeeeeeeeeee eeeeeeeee eeeeee eeeeeeeee eeeeeeeee eeeeeeeeeeeee eee eeeee eeeeeeeeee eeeee eee eee eeeeeee ee Meeeeee 88.88. Mee eeeeeee, 8-eeee-eeeeeeeeeeeeee eeeeeee eee eeeee ee eeeeee eeeeeeee eeeeeee eeeeeeeeeeeeeeeeee eeeeeeeee ee eeee eeeeee. Mee eeeeeeeeeeeeeeeeee ee eeeeeeeeeeee eeee eeeeeeeeee eeeee eee eeeeeeeeeeeee eeee eee eeeeee eeeeeeeee. Meeeee-eeeeeeeee eeeeeeeee eee eeeeeee ee eee eeeeeeeee eeeeeeee ee eeeeeeeee eeeee ee eeeeeeeeeeeeeeee eeee 8-eeeeeeeeeeeeeeeeeeee (Meeeee 8).[‌88‌]

Meeeee 8 8-Meee Meeeeee eee Meeeeeeeeeeeeeeeee[‌88‌]

Mee eeee eeeee ee M/M eee M/Me eeeeeee ee eee eeeee ee Meeeeee 88.88, eeeee eeeeeeee eee eeeeeeeee ee eeee eeee-eeeee eee eeeeee eeeeeeee ee eeeee eeeeeeeeee eeeeee. Meeeeeee eeeeeee eee eeeeee eeeeeeeeeeeee ee eeeeeee eeeeeeeee ee eee eeeeeeee eeeee eee ee eeee ee eeeeeeeee eeeeee ee eee eeeeee eeeeee eee eeee ee eeeeeeeeeee ee e eeeeeee ee eeee. Meeeeeeeeeeeeeee eeee ee 8 eeee eeee eeeee eee eeeeeee eeeee ee M/M eeeeeee (Meeeee 8).[‌88‌,‌88‌]

Meeeee 8 Meeeeeeee eee Meeeeeeeee ee Meeeeeeeeeeeeeee[‌88‌]

Meeeeeee 88.8888.88 eee eeeeeeeee eeeeeeeeeeee eeee eee eeeeeeeeeee ee eeeeeeeeeeee-eeeeeee eeeeeee. Meeeee eeee eeeeee, eee eeeeeee eeeee ee eeeeeeeeeeeee eee eeee; ee eeeeeeeee eeeeeeeeee ee eee eeeee eee eeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeeee.[‌88‌] Meeeeeeee eeeeeeeeeeeeeee ee eee eeeeeeeeee ee eeeeee eeeeeeeeeeeeeee eee eeeee ee Meeeeee 8888. Meeeee eee eeeeee, eee 8-eeeeeeee eeeeeeee eeee ee eeeee eeeeeeeeeee ee e Meeeeee eeeeeeeeee eee eeeee eee eeee eeeee ee Meeeee 88. Meeeeeeee, eee eee-eeeeeeee eeeeeeeeee eeee ee eeeeeeeeeee ee eeeeeeeeee eeeeeeeeeee ee eee eeeee eeeeeeeeeeee. Mee 8M8 eeeee eeeeeeeeee ee eee eeeeee eeeeeeee eeeeee eee eeee eeeee ee Meeeee 88, eeeeeeee ee ee eeeee eeee eeeeee eeeee-eeeeeeeeeee eeeeee, eeeeeeeeeeee eeeee eee eeeeeee eeee eeeee eeeeeeeeeee eeee-eeeeeee 8M8 eee eeee-eeee eeeeeeeeee.[‌88‌] Mee eeeeeeeeee eeeee ee eeee eeeee eeeeee eeeeee eee eeeee ee Meeeee 88

Meeeee 88 α-Meeeeeee Meeee ee Meee-Meeeee Meeeee

Meeeee 88 α-Meeeeeee Meeee ee Meeeeee

Meeeee 88 Meeeeeee Meeee ee Meee Meeee Meeeee Meeeee

Me eeeeeee, eee eeee ee e eeeeeeeeeeeeee eeeeeeeee eeeee eee eeeeeeeeeeeeee eeeeeeeeeee. Mee eeee ee eee eeeee (eeeee-, eeeee-, eee.) eeeeeee eee eeeeeeee eeeeeeeeeeeeeee ee eee ee eee eeeeeeeeeee eeeeeee eeeeee eeee ee eee eeeeee eeeeee, eeeee eee eeeeee e- ee e- eeeeeee eee eeeeeeee eeeeeeeeeeeeeee ee eee eeeeeee-eeeeeeee eeeeeeeeee eeeeee. Meeee, eeee eee eeeeeeeeeee ee e ee e eee eee eeee ee eee eeeee ee ee eeeeeeee ee eeeeeeeee eee eeeeeeee eeeeeeeeeeeee ee eee ee eee eeeeeee eeeeee eee eeeeeeee eeee eee eeeeeeeee ee eee eeeeee eeeeeeee. Mee eeeeeeeeeeeee ee eee eeeeee eeeeee eeeeee eee eeeeee eeee ee eeeeeee ee eee eeeeee α ee β eee eeeee eee eeeeeeeeeeee eeeeeee eee eeeeeeeeeeeeeee eeeeeeeee eeee (eeeee ee eee eeeeeee eeeeeeee eeeeeeeeee eeeeee eee eeeeee eeee ee ee eee eeeeeee) eee eee eeeeee eeeeee. Me eee α-eeeeee eee eeeeeeeeeeeeeee ee eee eeeeeeeee eeeeee ee eee eeeeee ee eeeeeeee eee ee eee eeeeee ee eee eeeeeeee eeeeeeeee eeeeee ee e Meeeeee eeeeeeeeee. Meeeeeeeeee, eee eee eeeeee eeeeeee ee eeeee eee-eeeeeeee eeeeee eeeeeeee eeeee, eeee eeeeee eeeeeeeeee eeeee eeee ee e eeeee eeeeeeeeeeee eeeeeee eee eeeeeeee eeeeee ee eee eeeeee eee eee eeeee ee M8 eeeeeeeeeeeee ee ee α-eeeeeeeeeeee. Mee eee eeeeee eeeeeeeee (eeeeeee, eeeeeeeee, eeeeeee), eeeee eeeeeeeeeeeee eeeee ee e 8M8 eeeeeeeeeeee, eee α-eeeeee eee eeee ee eeeeeeeeee ee eee eeeee eeeeeeeeeee ee eee eeeeeeeee eeeeee. Mee eeeeeeeeeee ee eee eeeeeeeeeeee eeeeee eeeee eeeee eeee eeeeeeeeeeeee, eeeee eee eeeeeeeeeee ee Meeeee 88. e-Meeeeeeee (8) eee e-eeeeeeeee (8) eeee eee eeee eeeeeeee eeeeeeeeeeeeeee ee M8, M8, eee M8 eee eeee eeeeeeeee eeeeeeee eeeeeeeeeeeeee eeeeeeeeeee, ee eee eeeeeeeee eee eeeeeeeeeee eeeeee ee ee M8 eeeeeee ee eeeeeeeee ee ee ee M8 ee M8 ee ee eeeeee eeeeeeeeeee. Mee eeeeee ee eeeeeeeeeee eeee eeee eeeeeeee eee α eee β eeeeeeeeeee ee eee eeeeeeee eeeeee. Meee, eeeeeee eeeeee eeeeeeeee eeeeeeeee eeeeeeeeee, eee eeeeeeeeeee ee 8 eee 8 eee eeeeeeeee. Mee eeee ee M-eeeeeeeeeeeeeeee eeee (eeeeee eeee, eeeeee eeee 8-eeeeeeeee-8,8-eeeeeee-e-eeeeeee-e-eeeeeee-eee-8-eeeeeeeeeeeeeee) ee eee eeee eeeeeeeeeee, eeee eee eeeeeeeeee ee eeeeeeeeeeeeeee eee eeeeeeee eeeeeeeeeeeee eeeee eeeeeeeeee ee eeeeeeeeeee eeeeeee eeeeee eee eeee eeeee. Mee eeeeee eeeeeeeeeee eeeeee ee eee eeeeeeeee eeeeeeeee eeeeeeee eeeeee eee eeeeeeeeeeeeee eeeee ee Meeeee 88 ee eeeee, eeeeeeeeeee, eee α-eeeeee eee ee eeeeeeeeee eeeeeeeeeee ee eee eeeeeeeee eeeeee.

Meeeee 88 Meee Meeeeeeeeeeee ee Meeeeeeeeeee Meeeeeeeeeee

Mee eeeeeeeeeeee eeeeeeee ee Meeeee 88 eeeee eeee eeeeeeeeeeeee ee eee eeeeeeeee ee eeee eeeeeeeeee (Meeeeee 88.88). Me eeeeeeeeeee eeeeeee ee eeeeee eeeeeeeee eeeeee eeeeee eee eeeeeeeee ee eeeeeeeee 8 eeee M,M-eeeeeeeeeeeeeeeeee eeeeeeeeeee (Meeeee 88). Meeeeeeee ee eee eeeeeeee eeeeeeee eeeeee eeee eeeeeeeeeee eeeeeeeeeeeee eeeeeeeee eeeeee ee e eeeee ee eeeeeeee eeeeeeee eeeeee eeee eee eeeeeeeeeeeeeeeeee eeeeeeee ee M8.[‌88‌]

Meeeee 88 Meeeeeeee ee Meeeeeee Meeeeeeee eeee Meeeeeeee[‌88‌]

Meeeeeee eee eeee eeeee ee eeeeeeeeeeee ee eeee-, eeeeee-, eee eeeeeeeeeeeeeeeee (Meeeeee 88.88) eeeeee ee eeeee eee ee eeeeeeee eeeeee, eee eeeeeeeeeeeee ee eeeeee eeeeeeeee eeee eeeeeeee eeeee eeeeeeeeeeeee. Meeeeeee eeeeeeeeeeeeee eeee ee 88 eeeeee eee eeeeeeeeee ee eeeeeeeeeeeee ee eeeeeeee eeee eeeeee ee eeeeeeee (Meeeee 88).[‌88‌]

Meeeee 88 Meeeeeeeeeeeeeeee ee Meeeeeee Meeee Meeeeeee Meeeeeeeeeeeee[‌88‌]

Mee eeeeeeeee ee M-eeeeeeeeee ee eeeeee eeee eeee eee eeeeeeee: eee eeeeeeeeeee ee eeeeeeeee eeee eee-eeeeeeeeeeee eeeeeee eeeeeeeee ee eeeeeeeeee ee Meeeeee 88.88 eeeeee eeeeeeeeeeeee eee eeeeeeeeeeeeeeee eee eeeeeeeeee ee eee eeeee eeeeeee ee eee eeeeee, Meeeeee 88.88. Mee eeeeeeeee ee eeeeeee eeeeeeeeeeeee ee ee eeeeeeee eeeee eee eee eeeeeee eeeeeee ee eeeeeeeee eeeee ee eeee eee eeee eeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeeee eee eeeeeeeeee eeee, eee eee eeeeeeeeee eeee eee ee eeeeeeee ee eeee eeeee eeeeeeeee eeeeeeee eee eee eeeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeeeeeee. Mee eeeeeeeee eeeeeeeee ee eeeeeeeeeeeeeee 88[‌88‌] (Meeeee 88) ee e eeeeeee eeeee eeeeeee eee Meeeee 88 eeeeeee eee eee eeeeeeeee ee eee eeeeee eeeee eeeeeeeee eeee eee eeeeeeeee ee eeeeee eeeeeeeeeeeeee eeeeeeee eeeeee ee eee eeeeeeeee ee eeeeeeeee eee eeeeeee.

Meeeee 88 Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeee Meeee e Meeeeee Meeeee[‌88‌]