Science of Synthesis

Constantieux, T.; Rodriguez, J., Science of Synthesis, (2005) 26, 422.

The base-induced fragmentation of cyclic 1,3-diol monosulfonate esters is probably the best illustration of the versatility of the Grob fragmentation. In 1965, Wharton,[‌43‌] by applying previous results,[‌49‌] developed a reaction for the selective construction of medium-sized ring enones. Under basic conditions, bicyclic cis- and trans-hydroxytoluenesulfonates ‌16A‌ and ‌16B‌, respectively, yield the monocyclic (5E)-cyclodec-5-en-1-one [(E)-‌17‌] while the cis-compound ‌16C‌ gives the (5Z)-cyclodec-5-en-1-one [(Z)-‌17‌] (‌Scheme 16‌).[‌43‌] However, the trans-compound ‌16D‌ gave neither (E)- or (Z)-‌17‌.

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‌Meeeee 88‌ Meeeee-Meeee Meee Meeeeeeee eee Meeeeee Meeeeeeeeeeee ee Meeeee 8,8-Meee Meeeeeeeeeeeeeeeeeeee[‌88‌]

Me eeeeeeeeeee ee eeeee eeeeeeeeee eeeeeee, eee ee eeeee eeeeeeeeeeeee,[‌88‌,‌88‌] Meeeeee eeeeeeeeeeeeee eeeeeee eeeeeee eeeeeeeeee eeeeeeee. Meeeeee, eeee eee eeeeeeeeeeeeee eeee eeeeee ee eee eeeeeeeeeeeeeee ee eee eeeeeee eeeee. Meeeeeeeeeee, eeee eee- eee eeeee-eeeeee eee­eeeeeee eee eeeeeeeeee eeee eeeeeeeeeeeeee eeeeeeee eeeeeeeee. Meeeeeee, eee eeeeee­eeeeeeeee ee eee eeeeeeee eeeee ee eeee ee eee eeeeeeeeeeeeeeeee ee eee eeeeeeeeeeeee. ­Meeeeee, eee eeeeeeeeeeeee eeeeeeee eeeee eeeeee eeee eeeeeeeeee ee eeeeeeeee eeeeee. Mee eeeee eeeeeee, eee eeeeeeee eee eeee eeeeee eeeeeee ee e eeeee eeeeee ee eeeeeee eeeeeee eeeeeeeee. Me eeeeeeeee eeeeee eeeeeeeeee eee eeeeeeeee eeeeeeeeeeee ee eeeeeeeeeeeee ee eeeeee 8,8-eeee eeeeeeeeeee.[‌88‌] Meee eeee eeeeee eeeeeeee eee eeeee eeee ee eeeeeeeeee eeee eeeeeeee.

Meeeee eeeeeeeeeeeeee eeeeee eee eeeee eeeeeeeee ee eee eeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee (‌88‌),[‌88‌–‌88‌] ee eee eeee eeeeeeee eeee eee eeeeeeeee eeeeeee ee eeee eeeeeee eeeeeee ee eeeeeeeee eeeee eee Meeeeee eeeeeeeeeeeee ee eee eee eeee (‌Meeeee 88‌). Meeeeeeee ee eee eeeeeee eeeeeeeeeeeeeeee eeeeeeeee ‌88‌ eeee eeee eeeeeeee ee eeee eeeeeee ee eeeeeee e eeeeeeeee eeeeeeeee eeeeeeeeeeee ‌88‌ ee eeee eeeee.

‌Meeeee 88‌ Mee Meee ee eee Meeee Meeeeeeee ee Meeeeeeeeeeeee[‌88‌]

Me e eeeee eeeeeeeee ee eeeeeeeeeeeee-M (‌88‌), e eeeeeeeee eeee eeeeeeeee eeeeeeee, Meeeeee eeeeeeee eee eee ee eeee eeeeeeeeeeeee ee eee eee eeee eee eee eeeeeeeeeeeeee eeeeeeeeeee ee eee eeee-eeeeeeee eeee.[‌88‌] Mee Meeeeee eeeeeeeeeeeee eee eeee eeee eeeeeeeeeeee eeeeeee ee eee eeeeeeeee ee eee eeee ee eee eeeeeeeee MM-888,888 (‌88‌) (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeee Meeeeee Meeeeeee Meeeeeeee eeeeeee Meeeeee Meeeeeeeeeeeee[‌88‌,‌88‌]

Meeeeeee eee Meeeeee eeeeeeeeeeeee eeeeeeeee eeeeeeee ee eeeeeeeee eeeeee, eeeeeeeeeeee eee eeeeee ee eeee eeeee eeeeee eee eeeeeeeeeee ee eee eeeeeeee eeeeeeeee.[‌88‌–‌88‌] Me eeeeeee eee ee eeeeeeeee eeee eeeeeee ee ee eeeeeee e eee-eee eeeeeee, e.e. ee eeeeeee eee eeeeeeeeeeeee ee eeeeeeeeeee eeee eeeeeee eeeeeeee eeeeeeeeeeeeee. Me ee eeeeeeeeeeee, e eeeeeee eeeeeeee ee eeeeeee[e.8.8]eee-8-eeeeee eeee e eeeeeeeeee eeeeee eeee eee eeee eeeeeeee. Meee eeeeeeee eeeeeeee e eeeeeeeeee eeee-eeeeeee eeeeeeeeee/Meeeeee eeeeeeeeeeeee (‌Meeeee 88‌).[‌88‌] Me eeee eeeeeee, eee eeeeeeeeeeeeeeeeeeeeeee eeeeeeee eeeeeeeee eee eee eeeeeeeeeeeee, ee eeeeeeeee ee eeee ee eeeeeeeeeeee ee eee eeeeeeeeeeeee eeeee eeeee ‌88‌ eeee eeeeeeeeeeeeeeeeee eeeeeeee. Mee Meeeeee eeeeeeeeeeeee ee eeeeeeee ee eee eee ee eeeeee eeeeeee ee eeeeeeeeeeeeeee eeeeeeeee eee eeeeeeee eeeeee ‌88‌. M eeeeee eeeeeeee eeeee eeeeeee eeeeeeeeeeeee (eeeee eeeeeeeee eeeeeeee eee 88-eeeee-8)[‌88‌] eeeeee eee eee ee eeeeeeee eeeee eeeeeeee eeeeeeeeee, eeeee eeeee eeeeeeee eeee eeeeeeeee eeeeeeeee ee eee α-eeeeeeee ee eee eeeee eeeeee eeeeeeee eeeee.

‌Meeeee 88‌ Meeeeeee Meeee Meeeeee Meeeeee Meeeeeeeeeeee[‌88‌,‌88‌]

Meeee eeeeeeee ee eeeeeeeee eeeeeeeeeee ee eeeeeeeeee ee eee Meee eeeeeeeeeeeee eeee eeeee eeeeeeee eeeeeeeeeeeeeee eeee eeee eeeeeeee ee eee eeeeeeeeee. Me eeee eeeeeee, ee eeeeeeeee eeeeeeeeeeeeeeee–eeeeeeeeeeeee eeeeeeee ee eeeeee-eeeee eeeeeeeeeee eeeeeee eee eeeeee eee eeee eeeeeeeee.[‌88‌] M eee eeeeeeeee eeeee eee eee eeeeeeeeeeee ee eee eeee ee eeeeeeeee eeeee eee eeee eeee eeeeeeee, eeeeeeeee e eee-eee Meeeeee eeeeeeeeeeeee–eeeeeeeee–eeeeeeeeeeeeeeeee eeeeeeee ee e eee eeee.[‌88‌] Me eeeeeeeee eeeeee eeeeeeee, eeeeee eeeee eee eeeeeeee eeeeee ee eeeeee eeeee eee eeee eeeeeeeeee ee eeee, eee eeee eeee eeeeeeeee. Meee, ee eeeeeeeeeeeeee Meeeeee-eeee eeeeeeee/eeeeeeeeeeeee eeeeeeee eeeeeeee ee eeeeeeee(MM) eeeeee eee eeee eeeeeeeee eeeeeeeee ee eeeeeeeee eeeeeeee ee eee eeeeeeeee ee eeeeeeeeeeeeee eee eeeeeeeeeeeee eeeeee-eeeee eeeeeeeeeee eeeeeee, eeee ee ‌88‌ eeee ‌88‌ eee eee eeeeeeee eeeeeeeee ‌88‌ (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meeeeeeeee Meeeeeeeeeeeee Meeeeee Meeeeeeeeee/Meeeeeeeeeeee Meeee Meeeeeee(MM) Meeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

(8M,8M,8eM,8M,8eM,88eM,88eM)-8-Meeeeee-8,8,8,8,88e-eeeeeeeeeee-8,8,8,8e,8,8,8e,8,-88e,88e-eeeeeeeee-88M-eeeeeeeeeeee[e,e]eeeeeee-88-eee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

M eeee ee eeeeeeeeeee eeeeeeeee ‌88‌ (88.8 ee, 8.88 eeee) ee eee e-MeMM (8 eM) ee 88°M eee eeeeeee eeee e-MeMM (88.8 ee, 8.88 eeee), eee eee eeeeeeeee eeee eee eeeeeee ee 88°M eee 88 eee. Mee eeeeeee eee eeeeeeeeeee eeeeeee Me8M (888 eM) eee eeeee (88 eM), eee eee eeeeeee eeeee eee eeeee (MeMM8), eeeeeeee, eee eeeeeeeeeeee. Mee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, eeeeeeeee eeeee/MeMMe 88:8) ee eeee eee eeeeeee ee e ­eeeeeeeee eee; eeeee: 88.8 ee (88%).

Meeeeeeeeee Meeeeee ‌88‌; Meeeeee Meeeeeeee:[‌88‌]

Me eeeee (888 ee, 8.8 eeee) eee eeeee eeeee e eeee ee M8 ee ee eeee-eeeee eeeee. MMM (88 eM) eee eeeee, eee eee eeeeeeeeee eee eeeeee ee eeeeeee –88 eee 8°M, eee MM8M8 (888 ee, 8.8 eeee) eee eeeee. Mee eeeeeee eee eeeeeee ee ee eee 8 e eee MeM8 (8 eee%) eee eeeee. Meeee eeeeeeee eee 8 eee, eee eeee eeee eeee eee eeeeee ee eee eeeeeeeee eeeeeeeeeee, eee eee eeeeeeeeeeeeeeee ‌88‌ (8 eeee) ee MMM (88 eM) eee eeeee eeee 8 eee. Mee eeeeeeee eee eeeeeeeeee, ee eee, eeee eeeeeee eeeee (888-M eeeeeee eeee) eeeee eeeeeee eee eeeeeeeeeee ee eee eeeeeeeeee eeeeeeeee eeeee. Meeee eee eeeeeeee eeeeeeee eee eeeeeeee (MMM ee MM eeeeeeee), eee eeeeeee eee eeeeee ee ee eee eeeeeee eee 8 e. Mee eeeeeeeee eeee eee eeeeeeee eeee e eee. ee eeee ee Meeeeeee'e eeee (eeeeeeeee eeeeee eeeeeeee) eee eeeeeeeee eeeeeee eeeee eeee Me8M. Mee eeeeeee eeeeeeee eeee eeeeee eeee eeeee eee eeeee (MeMM8). Mee eeeeeeee eeee eeeeeeee ee eeeee eeeeeeeeeeeeee.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 8888.