Science of Synthesis

Drabowicz, J.; Kiełbasiński, P.; Łyżwa, P.; Mikołajczyk, M., Science of Synthesis, (2008) 39, 551.

The thermal decomposition of sulfoxides that contain a β-hydrogen atom represents a general method for the synthesis of sulfenic acids. For example, di-tert-butyl sulfoxide (‌43‌; R1 = t-Bu) undergoes thermolysis at a relatively low temperature to give 2-methylpropane-2-sulfenic acid (‌44‌; R1 = t-Bu), together with isobutene (‌Scheme 18‌).[‌59‌] Other alkyl tert-butyl sulfoxides (e.g., ‌43‌; R1 = Me) can be pyrolyzed at rather high temperatures (100–200°C); in these cases, the flash-vacuum pyrolysis technique is used (‌Scheme 18‌).[‌60‌,‌61‌]

‌Meeeee 88‌ Meeeeeeeeee ee eeee-Meeee Meeeeeeeee[‌88‌–‌88‌]

Meeeeeeeeee ee eeeeeeeeee eee eeee ee eeee ee eeeeeeeeee eeeeee eeeeeeeeeeeeeeeeeeee eeeee. Mee eeeeeee, eeeeeee eee eeeeeeeee ‌88‌ (M8 = MMM) ee eeeee eeeeeee eee 88 eeeeeee eeeeeee ee eee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeee eeee ‌88‌ (M8 = MMM) ee 88% eeeee (‌Meeeee 88‌).[‌88‌] Meee eee eeeeeeeee eeeeee ‌88‌ (M8 = MMM, Me) eee eeeeeeee ee eeeeeee eeee e 888% eeeeee ee e eeeeeee ee eeeeeeeeeeeeeeeeeeeee eee eeeeeeeeeeeeeeeeeeee, eee eeeeeeeeeeeee eeeeeeeeeeeeee eeeeeeeeee ‌88‌ eee eeeeee ee eeeeee eeeeeeeeeeee eeeee (‌Meeeee 88‌).[‌88‌] Meeeeeeeee ee eeeee eeeeeeee ee eeeeeeeeee eeee eeeee eee eeeee eee eeeeeeeeeeeee eeeeeeee eeeee ‌88‌. Meee eee eeeeeeee ee eeeeeee eee ee eee eeeeeeee ee eeeee eeeeeee ee eeeeeeeeeeeee, eee eeeeeeeeeeeeee eeeeeeeee ‌88‌ (M8 = MMM) eee eeeeeeee eeee ‌88‌ (M8 = M) eee eeeeee eeeeeee eeeeee-eeee eeeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeee ee e eeeeeee eeeeeeeeeee eeeeeee eee eeeeeeeeee ‌88‌ eee eeeeeeee eeeee ‌88‌ ee eeeeeeeeeeee ee eee eeeeeeeee ee eee eeeeeeeeee eeeeeeee ‌88‌ eee ‌88‌ ee eeeeeeeee (88 eeeee) eeeeeee ee ‌88‌ (M8 = MMM) ee eeeeeee eeeeeeeeee eeeeeeeee eeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeeeeeeeeee Meeee[‌88‌–‌88‌]

Mee eeeeeeeee eeeeeeeee eeeeee eeeeeeee eeee ‌88‌ ee eeeeeeee eeee eee eeeeeeeee ‌88‌ eeee eeeeeee ee eeeeeee ee 88°M eee 88 e (‌Meeeee 88‌).[‌88‌] M eeeeeee eeeeee eee ee eeee eee eee eeeeeeeee ee eeeeeeee eeeee ‌88‌ eeee eeeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌–‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeee Meeee eeee Meeeeeeeee[‌88‌–‌88‌]

Meeeeeeeee ee eee Δ8-eeeeee eeeeeeeeeee ‌88‌ eeee e eeeee eeeeee ee eeeee eeeee eee eeeeeeeeeeeee eeeeeeee eeeee ‌88‌ eeeeeeee eeee eee eeeeeeeeeeeee eeeeeeeeeeeeee eeeeeeeee ‌88‌ ee eeeeeeeeee (‌Meeeee 88‌).[‌88‌,‌88‌]

‌Meeeee 88‌ Meeeeeeeee ee Δ8-Meeeee Meeeeeeeeee[‌88‌,‌88‌]

M eeeeeee ee eeeeeeee eeeee eee eeeeeeee ee eeeeeeeeeee ee β-eeeee eeeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌] Meee β-eeeee eeeeeeeeee eee ee eeee ee eee eeeeeeeee ee eee eeeeee ee eeeeee eeeeeeee eeeee ee eeeee eee eeeeeeeee ee eeeeeeeee eeee eee eeeee eeeeeeeeeee (‌Meeeee 88‌).[‌88‌–‌88‌]

‌Meeeee 88‌ Meeeeeeeeee ee β-Meeee Meeeeeeeee[‌88‌–‌88‌]

Me eeeeeeeee eeee eeeeeeee ee e M—M eeee ee eeeeeeee ee eee eeeeeeeeee eeeeeee eeeeeeeeee ‌88‌, eeeee eee eeeeee ee eeee eeee eee eeeeeeeeeeeee eeeeeeee ee eeeeeeeee ee eeeeeeeeeeeeeee ee –88°M. Me eeeeeee eee eeeeeeee ee eee eeeeeeeee ‌88‌ ee eeee eeeeeeeeeee, eee eeeeeee ‌88‌ eee eeeeeeee eeeee ‌88‌ eee eeeeeeeee ee eeeeeeeeeee M—Mα eeeeeeee (‌Meeeee 88‌).[‌88‌] Mee eeeeeeeee ee eeee eeeee eee eeee eeeeeeeee ee eeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeee eee ee eeeeeeee eeee eeeeee eeeeeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeee ee Meeeeeeeee Meeeeee Meeeeeeeee[‌88‌]

Mee eeeeeeeeeeeee eeee ‌88‌ ee eeeeee ee ee eeeeeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeeee eeeee-eeeeeeeeeeeeeeee 8-eeeee (‌88‌) (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee eeeee-Meeeeeeeeeeeeeee 8-Meeee[‌88‌]

Mee Meeee–Meeee eeeeeee eeeeee ee eeeeeee eeeeeeeeeeeee ee eee eeeeeeeeeeeeeeee ‌88‌ ee eeeeee ‌88‌ eeeeeeeeeeeeeee eeeee eeee ee eeeeeeeeeeeeee eeee (‌88‌) eee eee eeeeeeeeeeeee eeeeeeeee-8,8-eeeee eeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeeeeeee Meee[‌88‌]

Meeeeeeee ee 8-(eeee-eeeeeeeeeeeee)eeeeeeeeee (‌88‌) eeeee eee eeeeeeeeeeeee eeeeeeeee ‌88‌, eeeee eeeeeee eeeeeeeee ee Me-eeee eeeeeeeeeee ee eeee eee eeeeee eeeeeeeeee-8-eeeeeeee eeee (‌88‌) (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeeeeeee-8-eeeeeeee Meee[‌88‌]

Mee eeeeeeee eeeeeeeee ‌88‌ eeeeeeeee e eeeeee eeeeeeeee eeeeeeeeeee–eeeeeeeeeeeeee eeeeeeee eeee eeeeeeee ee eeee eee eeeeee eeeeeeeee ‌88‌ eeee e eeee eeeee ee eeeee- eee eeeeeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ M Meeeee Meeeeeeee Meeeeeeeeee–Meeeeeee Meee Meeeeeee[‌88‌]

M eeeeeee eeeeeeeeeeeeee eeeeeeeeeee ee eeee ee eee eeeeeeeee ee eee eeeeee eeeeeeeeee ‌88‌ eee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeee ee Meeeee Meeeeeeeee[‌88‌]

Meeeeeeeeeeeee ‌88‌ eeeeeee eeeeeee eeeeeeeeeeeee eeeee eeeeee eeeeeeeeee eeee eeeee eeeeeeee eee eee eeeeeeeeeee ee eeeeeeeeee ee eeee eeeeeeeeeeeeee eeeee ‌88‌ (eeeee eee ee eeeeeee ee eeeeeee ee eeeeeee) (‌Meeeee 88‌).[‌88‌] Meee eeee eeee-eeeee 8-eeeeeeeeeeeee-8-eeeeeeeeeeeee (‌88‌) eeeee 8-(eeeeeeeeeeeeeeeee)-8-eeeeeeeeeeeee (‌88‌), eeeee ee eeeeeee ee eeeeeeeeeeeeeee ee eeee eee eeeeeeeeeeeee eeeeeeeeeeeee ‌88‌.[‌88‌]

‌Meeeee 88‌ Meeeeeeeeeeee ee Meeeeee Meeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

Meeeeeeeee[8.8.8.88,8.88,88.888,88]eeeee-8,8,8,8,88,88,88,88,88-eeeeeee-8-eeeeeeee Meee (Meeeeeeeee-8-eeeeeeee Meee, ‌88‌):[‌88‌]

M eeee ee eeeeeee ‌88‌ (8.88 eeee) ee MM8Me8 (88 eM) eee eeeeeee eeee MMMMM (8 eeeee) ee MM8Me8 (88 eM) ee 8°M eee eee eeeeeee eee eeeeeee eee 88 e eeeee eeeeeee ee 88°M. Mee eeee eee eeeeee ee MeMMM8 eee eeeeeeeee ee e eeeeee eeeeee, eeeeeeeee eeeeeeeeeee MMM (eeeeee/MM8Me8 8:8); eeeee: 88.8%; ee 888–888°M (eee).

References

Meeeeee Meeeeeeeeee

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