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Please login or sign up for a free trial to access the full content. Variation 1: O,O-Acetals

DOI: 10.1055/sos-SD-030-00101

Takeda, T.; Tsubouchi, A.Science of Synthesis, (200730134.

Dithioacetals are prepared from acetals by transthioacetalization with thiols in the presence of acid catalysts, similarly to the thioacetalization of aldehydes and ketones. The transthioacetalization generally enjoys an advantage over the thioacetalization in that the reaction process is more rapid and cleaner. Thus, protic acids, metal salt based Lewis acids, and other Lewis acids are considered as catalysts for this purpose. Without a catalyst, these transformations are carried out by heating the acetals with excess thiols.

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Meeeeeee M8 M8 M8 M8 Meeeeeeeee Meeee (%) Mee
MeMM M Me Me Me eeeeeee 88 [‌88‌]
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Meeeeeee Meeeeeeeee Meeeeeeeeeee Meeee (%) Mee
MeMeM8 8M ee Me8M, ee, 8888eee M8=M; M8=eMe, Me, 8-MeMM8M8, 8,8-(MeM)8M8M8, MM=MMMe; M8=Me, Me; M8,M8=(MM8)8; M8=Me, Me; M8=M8=Me, Me; M8=Me; M8,M8=(MM8)8; M8=Me, Me 8888 [‌88‌,‌88‌]
MeMe8 8.8 eeeee, Me8M, ee, 88eee M8=M; M8=Me, (MM8)8Me; M8=Me; M8=Me, Me 8888 [‌88‌]
Me(MMe)8 8eee%, [eeee]MM8,e ee, 888eee M8=M; M8=8-MM8M8 (M=M, Me, MMe), MM=MMMe; M8=Me, Me, Me; M8=Me 8888 [‌88‌]
MeMe8 MMMMe, MeMM M8=M; M8=MMMeMe; M8=M8=Me 88 [‌88‌]
MeMe8 8eee%, 8,8-eeeeeeeeeeeeee, eeeeee, 888eee M8=M; M8=Me, 8-M8M=MMMM8MM8M8, MM=MMMe; M8=Me, Me; M8,M8=(MM8)8; M8=Me, e-Me, Me; M8=Me; M8=eMe; M8=Me; M8=Me 8888 [‌88‌]
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Meeeeeee Meeeeeeeee Meeeeeeeeeee Meeee (%) Mee
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Mee(eeeeeeeeeeeeee)eeeeeee (8, M8=M8=M; M8=Me); Meeeeee Meeeeeeee:[‌88‌]

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8-[8,8-Mee(eeeeeeeeeeeeee)eeeee]-8-eeeee-8,8,8,8,8,8-eeeeeeeee-8,8-eeeeeeeeeeeeee[8,8-e]eeeeee (88):[‌88‌]

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