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30.3.3.1.8.4 Variation 4: Catalyzed by Halogens and Derivatives

DOI: 10.1055/sos-SD-030-00185

Leung, M.-k.; Luh, T.-Y.Science of Synthesis, (200730299.

The use of halogens and derivatives to promote dithioacetalization has been extensively studied. The reactivity of acetals derived from ketones is usually higher than those of aldehydes under these reaction conditions. Iodine in chloroform is an efficient catalyst for the dithioacetalization of O,O-acetals 160 to give 1,3-dithiolanes 161 (Scheme 86).[‌231‌] The tetrahydropyran group remains intact in competitive reactions while 2-hydroxybenzaldehyde is quantitatively transformed to the corresponding 1,3-dithiolane.

Meeeee 88 Meeeee-Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeee 88

M,M-Meeeee Meeee (%) Mee
88 [‌888‌]
88 [‌888‌]
88 [‌888‌]

Me eeeeeeeee eeeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 eee ee eeeeeeeee eeeee M-eeeeeeeeeeeeeeee ee eeeeeeeeeeeeeee ee eeee 8,8-eeeeeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 M-Meeeeeeeeeeeeeee-Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 eeee eeeeee-8,8-eeeeeee ee eeeeeee 8,8-eeeeeeeeeee 888 eee ee eeeeeeee ee eeeee 8,8,8,8-eeeeeeeeeeeeeee-8,8-eeeeeee (MMMMM) ee eee eeeeeeee ee eeeeeeeeee ee eeee eeeeeeeeeee (Meeeee 88).[‌888‌] Mee eeeeee eeeeeee eeee eeeeeeeeeeee ee eeee eeeeeeee ee eeeeeeeeee ee eeeeeee eeeeeee eeee eeeeeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee Meeeeeeee ee8,8,8,8-Meeeeeeeeeeeeee-8,8-eeeeeee[‌888‌]

Mee eeeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 ee 8,8-eeeeeeeeeee 888, eeeeeee ee eeeeeeeeeeeeeeeeee eeeeeeeeee, ee eeeee eee eeee (Meeeee 88).[‌888‌] Meeeee eeeeeeee eeeee eee eeeeeeee eeee eeeeeeee eeeeeee eeeeeeeeee eeeeeeee-eeeeeeeee eeeeeeeeeeee eee eeee. Me eeee ee 8,8-eeeeeeeeee 888, 8,8-eeeeeeee eee eeee ee eeee ee eeeeeeee eeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeee Meeeeeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 Meeee (%) Mee
M Me 88 [‌888‌]
M 8-MeMM8M8 88 [‌888‌]
M 8-MMM8M8 88 [‌888‌]
M 8-M8MM8M8 88 [‌888‌]
M 8-MeM8M8 88 [‌888‌]
M 8-M8MM8M8 88 [‌888‌]
M 8-eeeee 88 [‌888‌]
M (M)-MM=MMMe 88 [‌888‌]
Me Me 88 [‌888‌]
(MM8)8 88 [‌888‌]

Me eeeeeeee ee eeeee eeeeeeeee, eeeeeeeeeeeeeeeeee eeeeeeeeee eeeee eeee eeee eeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeee ee eeeeeee eeeeeee eeee eeeeeeeee eeeeeeee ee eeeee eeee eeeeeee (Meeeee 88).[‌888‌] Me eeeeeeee, eeeeeee eeeeeeeeee eeeeeeee-eeeeeeeeeee eeeeeeeeeeee eeeee eeeeee eeee eeeee eeeeeeeeee eeeeeeee-eeeeeeee eeeeeeeeeeee, eee eeeeeeeeeeeeeee eeeeee eee eeee eeee eeeeeeee eeee eeeeee eeeeeee.

Meeeee 88 Meeeeeeeee ee Meeeeeeeeee ee Meeeeeeee Meeeeee[‌888‌]

M,M-Meeeeee 888 eee ee eeeeeeeee eeee 8,8-eeeeeeeeeee 888 ee eeeee eeeee(eeeeeeee)eeeeeeeee eeeeeee ee eee eeeeeeee eeeee eeeeeee-eeee eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeee(eeeeeeee)eeeeeeeee Meeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Me eee eeeeeeee ee eeeeeeeeeeeeeeeeeeee eeee, M,M-eeeeeee eee eeeeeee eeeeeeeee eeee eeeee 8,8-eeeeeeeeeee, e.e. 888, ee eeeeeeeee eeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeeeeee Meee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Me eeeeeeee, eee eeeeeeeeee eeeeeeeeeeeeeeeeeee ee ee M,M-eeeeee eeeee ee eee eeeeeeee ee e eeeeee eeeee eeeeeeee eeee eee eeeeeeeeee ee M,M-eeeeeee ee eeeeeeeeee eeeeee eeeee eeeee eeeeeeeeee (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeee Meeeeeee ee ee M,M-Meeeee Meeee ee eee Meeeeeee ee e Meeeee Meeee[‌888‌]

Meeeeee eeeeeeee ee eeeeee eee (eeee eeeee ee eeeeee eeeeeeee) ee eeeee eee eee eeeeeeeeee ee M,M-eeeeeee 888 eeee 8,8-eeeeeeeeeee 888 (Meeeee 88).[‌888‌]

Meeeee 88 Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee Meeeeeeee ee Meeeeee Meeeeeee ee Meeeee Mee[‌888‌]

Meeeeeeeeeeeeeeeee eeeeeee ee e eeeeee eeeee ee e eeee eeeeeeeee eee eeeeeeeeee eeeeeee eee eee eeeeeeeeeeeeeeeeeee ee M,M-eeeeeee 888 ee 8,8-eeeeeeeeeee 888 eeeee eeeeeee-eeee eeeeeeeeee (Meeeee 88).[‌888‌] M eeee eeeee ee eeeeeee eee eeeeeee eeee eeeee eeeeeeeeeeeeee. Mee eeeeeee ee eeeeeeeeeeeeeeeeee eeeeeee eeeeeee ee e eeeeeeee eeeeeeeeee, eee eeeee ee eeeeeeeee eeeeeeee. Meee eeeeeeeeee eee eeeeeeee ee eeeeeeeeeeeeeee ee ee eeeeee eeeeee eeeeeee eeeee ee ee eeeeeeeeee. Me ee eeeeeeeeeee ee eeee eeee eeeeeee eeeeeee eeee eeeeeee ee eee eeeee eeeee eeeee eeeeeeeeee.

Meeeee 88 Meeeeeeeeeeeeeeeee Meeeeee Meeeeeeee Meeeeeeeeeeeeeeeeee ee M,M-Meeeeee[‌888‌]

Meeeeeeeeee 88

M8 M8 M8 Meeee (%) Mee
Me Me Me 88 [‌888‌]
Me (MM8)8 88 [‌888‌]
8-M8MM8M8 (MM8)8 88 [‌888‌]
8-MeM8M8 (MM8)8 88 [‌888‌]
8-MeMM8M8 (MM8)8 88 [‌888‌]
8-(M8M=MMMM8M)M8M8 (MM8)8 88 [‌888‌]
Me (MM8)8 88 [‌888‌]
(M)-MM=MMMe (MM8)8 88 [‌888‌]
(MM8)8Me (MM8)8 88 [‌888‌]
(MM8)8Me Me Me 88 [‌888‌]

Meeeeeeeeeee Meeeeeeee

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeee:[‌888‌]

M eeeeeee ee eee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (88eeee), eee M8 (8.88e, 8.8eeee) ee MMMe8 (88eM) eee eeeeeee ee ee, eee eeeeeeee eeee 8.8M Me8M8M8 (88eM) eee 88% MeMM (88eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee M-Meeeeeeeeeeeeeee:[‌888‌]

M eeeeeee ee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.8eeee), eee MMM (88eee%) ee MM8Me8 (88eM) eee eeeeeee ee ee, eee eeeeeeee eeee 8M MeMM. Mee eeeeeee eeeee eee eeeeeeeee, eee eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8. Mee eeeeeeee eeeeeee eeeeeeee eeee eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee 8,8,8,8-Meeeeeeeeeeeeee-8,8-eeeeeee:[‌888‌]

M eeeeeee ee eee M,M-eeeeee 888 (8eeee), 8,8,8,8-eeeeeeeeeeeeeee-8,8-eeeeeee (88eee% eee eeeeeee eeeeeee eeee eeeeeeeee, 88eee% eee eee eeeeee eeeeeee eeee eeeeeeeeeeee, eee 88eee% eee eee eeeeee eeeeeee eeee eeeeeeeeeeee) eee eeeeee-8,8-eeeeeee (8.8eeee eee eeeeeee eeeeeee eeee eeeeeeeee, 8.8eeee eee eee eeeeee eeeeeee eeee eeeeeeeeeeee, eee 8.8eeee eee eee eeeeee eeeeeee eeee eeeeeeeeeeee) ee MMMe8 (8eM) eee eeeeeee ee ee, eee eeeeeeee eeee 8% MeMM (88eM). Mee eeeeeee eeeee eee eeeeeeeee eee eee eeeeeee eeeee eee eeeeeeeee eeee MMMe8 (8×88eM). Mee eeeeeeee eeeeeeee eeee eeeeee eeee eeeee eee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeeeeee eeeee/MeMMe 8:8); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeee Meeeeeeeee:[‌888‌]

M eeeeeee ee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.8eeee), eee eeeeeeeeeeeeeeeeee eeeeeeeeee (8.88eeee) ee MeMM (8eM) eee eeeeeee ee ee, eee eeeeee eeee eee. MeMMM8 (88eM). Mee eeeeeee eee eeeeeeeee eeee MeMMe (8×88eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee; eeeee: 8888%.

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

M eeeeeeeee eeeeee ee Me8MMe+Me (8.888.88eee%) eee eeeee ee e eeeeeee ee eee M,M-eeeeee 888 (8eeee) eee eeeeee-8,8-eeeeeee (8.8eeee), eee eee eeeeeee eee eeeeeee ee ee. Meeee eeeeeeeeee ee eee eeeeeeee, eee eeeeeee eee eeeeeeeeeee eeee 8 eeeee ee eee. MeMMM8 eeee. Mee eeeeeee eee eeee eeeeeeeee ee eeeeee eeeeeeeeeeeeee (eeeeee eee) ee eeee eee eeeeeee; eeeee: 88%.

8,8-Meeee-8,88-eeeeeeeeeeeee[8.8.8.8]eeeeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

M eeeeeee ee 8,8,8,88-eeeeeeeeeeeeeee[8.8.8.8]eeeeeeeeeee (8.8e, 8eeee), eeeeee-8,8-eeeeeee (8.8eM, 8.8eeee), eee eeeeeeeeeeeeeeeeeeee eeee (8.88e, 8.8eeee) ee MMMe8 (88eM) eee eeeeeee ee ee, eee eeeeee eeee 88% MeMM (88eM). Mee eeeeeee eee eeeeeee eeee MMMe8 (88eM) eee eee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee M8M, eeeee (Me8MM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88%; ee 888888°M (eeeeeeeee eeeee/MeMMe 8:8).

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeee Meeeeeee ee Meeeee Mee:[‌888‌]

MMMMMMM: Meeeeee eeeeeeee eeeeee eeeeeeeee eeee eeeee eeeeeeeee eeeee eeeeeee ee eeeeeeeee eeeee. Me ee eeeeeeeee eeeeeeeeeee ee eee eeeeeee.

M eeeeeee ee eee M,M-eeeeee 888 (8eeee), eeeeee-8,8-eeeeeee (8.8eeee), eee MMMe8 ee eeeeee eee (8.88.8e) ee MMMe8 (88eM) eee eeeeeee ee ee eee 8888eee eee eeeeee eeee 88% MeMM (88eM). Mee eeeeeee eee eeeeeee eeee MMMe8 (88eM). Mee eeeeeee eeeee eee eeeeeeeee, eeeeee eeee M8M, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeeeeeeee (eeeeeeeee eeeee); eeeee: 8888%.

8,8-Meeeeeeeeee 888; Meeeeee Meeeeeeee Meeee Meeeeeeeeeeeeeeeee Meeeeee:[‌888‌]

M eeeeeee ee eee M,M-eeeeee 888 (8.8eeee) eee eeeeee-8,8-eeeeeee (8.8eeee) eee eeeee ee eeeeee MMMM (8.88e, 8.8eeee) ee 888888°M. Mee eeeeeee eee eeeeeee ee 888888°M eee eeeeeeeee eeee Me8M. Mee eeeeeee eeeeeee eee eeeeee eeee 88% MeMM, eeeee, eeeee, eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeee eeeeeeee ee eeeeee eeeeeeeeeeeeee; eeeee: 8888%.

References


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