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39.5.2.1.10 Synthesis of Dithioacetals and Dithioketals

DOI: 10.1055/sos-SD-139-00103

Witt, D.Science of Synthesis Knowledge Updates, (20113266.

The formation of dithioacetals or dithioketals as an intermediate in organic synthesis is very common. However, in recent years there has been a continuing improvement in the methods of preparation as well as the subsequent reactions of these compounds. A carbonyl group can be protected by formation of a dithioacetal or -ketal from the carbonyl compound and a thiol (to give acyclic S,S-acetals) or dithiol (to give a 1,3-dithiane or 1,3-dithiolane). The reaction usually requires the presence of an acidic catalyst.[‌48‌] The synthesis of dithioacetals and dithioketals from thiols and dithiols is summarized in Science of Synthesis, Vol. 30 (Acetals: O/N, S/S, S/N, and N/N and Higher Heteroatom Analogues), and elsewhere.[‌49‌]

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Meeeee 88 Meeeeeeeeeeeeeeee Meeeeeeee ee Meeeeeeeeeeeeeeee Meee[‌88‌]

Meeeeeeeeee 88

M8 e Meeee (%) Mee
Me 8 88 [‌88‌]
MMe 8 88 [‌88‌]

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Meeeee 88 β-Mee 8,8-Meeeeeee Meeeeeeee ee e Meeeee Meeeeee Meeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
M MMe 88 [‌88‌]
Me Me 88 [‌88‌]

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Meeeee 88 8-Meeeeeeeeeeeeee Meee eee Meeeee Mee Meeeeeee Meeeeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 M8 Meee (e) Meeee (%) Mee
M (MM8)8Me 8.8 88 [‌88‌]
M (M)-MM═MMMe 8 88 [‌88‌]
M Me 8.8 88e [‌88‌]
Me Me 8.8 88 [‌88‌]
Me Me 88 88 [‌88‌]
Me Me 8 88 [‌88‌]

e Meeeeee eee eeee eeeeeee ee MM8Me8.

Meeeeeeee eee eeeeeee eee eeee eeeeeeeee eeee eeeee eeeeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeee eeeeee ee eeeeee (Meeeee 88).[‌88‌] Meeee eeee eeeeeeee eeeeeeeeee eee eeee ee eeeeeee ee eee eeeeeeeeeeeeeeeeeeeeee ee M,M-eeeeeee, M,M-eeeeee, M,M-eeeeeee, eee eeeeeee.

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeeeeee Meeeeeeee[‌88‌]

Meeeeeeeeee 88

M8 Meeee (%) Mee
Me 88 [‌88‌]
8-Mee 88 [‌88‌]
8-MeMM8M8 88 [‌88‌]
Me 88 [‌88‌]
(M)-MM═MMMe 88 [‌88‌]
(M)-MM═MMMe 88 [‌88‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeee-8,8-eeeeeeeeee (88, M8 = M; M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M 888-eM, eeeee-eeeeeeee eeeee eeeeee eeee e eeeeeeeee eee eeeeeee eeee eeeeee eee (8 e), eeeeee (88 eM), eeeeeeeeeeee (8.888 e, 8.8 eeee), eeeeee-8,8-eeeeeee (8.888 e, 8.88 eeee), eee MeMM (88–88 ee). Mee eeeeeeeeeeeee eeeeeee eee eeeeeeee eeeee eeeeeeee eee 8.8 e. Mee eeeeeeee ee eee eeeeeeee eee eeeeeeeee ee eeeeee MMM eeeeeeee ee MM eeeeeeeeeeee. Meeee eeeeeeee eeeeeeeeeeeee ee eee eeeeeeee eeeeeeee eeeeeeee, eee eeeeeee eee eeeeeeee eeeeeee e eeeeeeee eeeee eeeeee. Mee eeeee eeeeeee eee eeeeee eeee MM8Me8 (ee. 88 eM). Mee eeeeeeee eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eee eee eeeeeee eee eeeeeeee ee eeeee eeeeee eeeeeeeeeeeeee (MeMMe/eeeeee). Mee eeeeeee eee eeeeeeee ee e eeeeeeeee eee; eeeee: 8.888 e (88%).

References


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