Science of Synthesis

Leung, M.-k.; Luh, T.-Y., Science of Synthesis, (2007) 30, 285.

Enamines, imines, and related functionalities can also undergo reaction with ethane-1,2-dithiol to give the corresponding 1,3-dithiolanes. As expected, these imine-like structures are less reactive than the carbonyl analogues. Similar to alkyl enol ethers, enamines ‌121‌ can be transformed into 1,3-dithiolanes ‌122‌ by dithioacetalization in the presence of appropriate catalysts (‌Scheme 63‌).[‌243‌] Although activation of basic nitrogen-containing compounds by Lewis acids is usually incompatible, kaolinitic clay catalysts are shown to promote dithioacetalization.

‌Meeeee 88‌ Meeeeeeeee Meee Meeeeeeee Meeeeeeee ee Meeeeeee eeee Meeeee-8,8-eeeeeee[‌888‌]

M eeeeeee ee eeeeeeeee eee eeeeeeeee eeeeeee eeeeeeeeeeeeeeeeeee eeee eeeeee-8,8-eeeeeee ee eee eeeeeeee ee eeeeeeeeee eeee; eee eeeeeee, eeeeee ‌888‌ eeeeeee eee eeeeeeeeeeeee 8,8-eeeeeeeeeee ‌888‌ ee eeee eeeee (‌Meeeee 88‌).[‌888‌] Mee eeeee eeeeeee eeee eeeeeeeeeeeeee eeee eeeee eeeeeeee eeeee eeeee eeeeeeeeee; eeeeeee, eeeeeeee eeeeeeeee eeee ee eeeeee eee 8,8-eeeeeeeeee eeeeeeee.

‌Meeeee 88‌ Meeeeeeeee Meee Meeeeeeee Meeeeeeee ee Meeeee eeee Meeeee-8,8-eeeeeee[‌888‌]

‌Meeeeeeeeee 88‌

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

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeee eeee Meeeee-8,8-eeeeeee Meeeeeeee ee Meeee Meeeeeeeeee–Meeeeee Meeee Meeeeee[‌888‌]

‌Meeeeeeeeee 88‌

Meeeeeeee	Meeee (%)	Mee
	88	[‌888‌]
	88	[‌888‌]
	88	[‌888‌]
	88	[‌888‌]
	88e,e	[‌888‌]
	88e	[‌888‌]
	88	[‌888‌]

e Mee eeeeee eeeee eee eeee eeeeeeeee eeee e 8,8-eeeeeeeeee.

e Mee eeeeeeeeeeee eeeeee ee eeee 88% eee eeeeeeeeee.

e Mee eeeeeeeeeeee eeeeee eee eeee 88%.

Me ee eeeeeeeeee eeee eeeeeeeeee eeee ee ee eeeeeeeee eeeeeeee ee eeeeeee eeeeeeeeeeeeeee eeee 8,8-eeeeeeeeeee ee eeee eeeee (‌Meeeee 88‌).[‌888‌]

‌Meeeee 88‌ Meeeeeeeee Meee Meeeeeeee Meeeeeeee ee Meeeeeeeeeeeeee eeee Meeeee-8,8-eeeeeee[‌888‌]

Meeeeeeeeeee Meeeeeeee

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

Mee eeeeeee ‌888‌ (88 eeee), eeeeee-8,8-eeeeeee (88 eeee), eee eeeeeeeeee eeee (88% ee eeeeee ee eee eeeeeeee eeeeeeee) ee MMe8 (MMMMMMM: eeeee) eee eeeeeeee eee 8–8 e. Mee eeee eeeeeeee eee eeeeeeee eee eee eeeeeeee eee eeeeee ee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88–88%.

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

Mee eeeee ‌888‌ (88 eeee), eeeeee-8,8-eeeeeee (88 eeee), eee eeee (88% ee eeeeee ee eee eeeeeeee eeeeeeee) ee MMe8 (MMMMMMM: eeeee) eee eeeeeeee eee 8–8 e. Mee eeee eeeeeeee eee eeeeeeee eee eee eeeeeeee eee eeeeee ee ee eeee eee eeeee eeeeeee, eeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee; eeeee: 88–88%.

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

Me e eeee ee eee eeeeeeeee ‌888‌ (8 eeee) ee eeeee MM8Me8 (8 eM) ee 8°M eee eeeee eeeeee-8,8-eeeeeee (888 μM, 8.8 eeee) eeeeeeee ee MM8•MMe8 (888 μM, 8 eeee), eeeee ee eeeee eeeeeeeeee. Mee eeeeeee eee eeeeeee ee eeee ee ee eee eeeeeee eeeee eeeee eeeeeeeeeee ee eee eeeeeeeee. Mee. MeMMM8 eee eeeee, eee eee eeeeeee eeeee eee eeeeeeeee, eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeee ee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/Me8M); eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8, 888.
• 8.Meeeee-Meee, (8888) M 88e, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.