Science of Synthesis

Soenen, D. R.; Vanderwal, C. D., Science of Synthesis, (2008) 37, 122.

Like alkyl-substituted cycloalkenes, the reactivity of phenylcycloalkenes toward photoalkoxylation depends on ring size. Irradiation of methanolic solutions of 1-phenylcycloalkenes ‌151‌ (‌Scheme 20‌) shows that alcohol addition to give ethers ‌152‌ only occurs to 1-phenylcyclohexene and 1-phenylcycloheptene, presumably by thermal addition of methanol to the trans-phenylcycloalkenes formed from the orthogonal excited states of ‌151‌ (n = 2) and ‌151‌ (n = 3). Formation of trans-phenylcyclopentene is presumably precluded by its inherent ring strain, and trans-phenylcyclooctene does not suffer enough strain to lower the energy barrier for methanol addition.[‌94‌]

‌Meeeee 88‌ Meeeeeeeeeeee Meeeeeeeeeee ee Meeeeeeeee Meeeeee[‌88‌–‌88‌]

Meeeeeeeee eeeeeee eeeeeee ee eeeeeee eeeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeee. Me eeeeeee, eee eeeeeee eeee ee ee eeee-Meeeeeeeeee eeeeeee; eeeeeee, eeeeeee eeeeeeee ee eee eeeeeeee eeeeeeee (Meeeeeeeeee eeeeeeeeeeeeeeee) eeee eeeee eeee eee eeeeeeeeee eeee eeeee ee eeeeeeee eeee. Mee eeeeeee, eeeeeeeeeee ee 8-eeee-8-eeeeeeeeeee (‌888‌) ee eeeeeeee eeeeeeee eeeeeeee eeeeee eeeee ‌888‌ ee eeeeeeeeeeee eeeee (‌Meeeee 88‌).[‌88‌] Me eeeeeee eeeeeeee ee 8-eeeeeeeeeeeee (‌888‌), eeee eeeeeeeeee ee e 888-M eeee-eeeeeeee eeeeeee eeee ee eee eeeeeeee ee eeeeeeeee eeee, eeeeeeeee eeee eeeeeeeeeeee eeeeeeee ee eeeeeee eee eeeeeeeeeeeee eeeee eeeee ‌888‌ eee eeeeee-eeeeeeee eeeeeeee ee eeeeeee 8-eeeeeeeeeeeee (‌888‌) (‌Meeeee 88‌). Me eeeeeeee, 8-eeeeeeeeeeeee eeee eee eeeeeee eeeeeeee eeeee eeeeeee eeeeeeeeee.[‌88‌] Mee eee ee eeeeeeeeeee-8-eeeeeeeeeeee ee eeeeeeeeeeeeeee ee eee eeeeeeeeeeeeeeeee ee 8,8-eeeeeeeeeeeeee eeeeeeeee eeeeeeeeeeeeeee eeeeeeeeeeeee ee eee eeeee eeeee eeeeeee. Me eeee, 8,8-eeeeeeeeeeeeee eeeeee eeee eeeeeeee, eeeeee-8-ee, eee eeee-eeeee eeeeeee ee eeeeee eee eeeeeeeeeeeee eeeee 8,8-eeeeeeeeeeeee eeeeee ee 88, 88, eee 88% eeeeee, eeeeeeeeeeee.[‌88‌] Mee eeeeeeeeee ee eeeeeeee eeeeeeee ee 8,8-eeeeeeeeeeeeee, 8,8-eeeeeeeeeeeeeee, eee e 8-eeeeeeeeeeeeeeeeee eeee eeeeeeeeee-8,88-eeeeeeeeeeeeee ee eeeeeeeeeeeeeee ee eeeeeeeee ee eeeeeee eeeeeeee.[‌88‌]

Mee eee ee eeeeeeeeeeeeeee eeeeee eeeeeeeeeeee eeeeeeeee eeeeeeee ee 8-eeeee-8-eeeeeeeeeeeee ee eeeeeee eee eeee-Meeeeeeeeee eeeee eeeeeeee. Meeeeeeeeeee eeeeeeee ee e eeeeeee ee eeeeeeee ee 8-eeeee-8-eeeeeeeeeeee (‌888‌) eeee eee eeeeeee eeee eeeeeeeee ee eeee eeeeeee; ee eeeeeeee ee eeeeeee eeeeeeee ee eee eeeeeeee ee 88% eeeeeeeee ee eee eeeeeee eeeeeeee eeeeeee eee eeeeeeeeeeeee eeeee eeeee eeeeeee ‌888‌ ee 88–88% eeeee (‌Meeeee 88‌). 8-Meeee-8-eeeeeeeeeeeee eeee eeeee eeeeeeeeeeee ee eee 8-eeeeeeee ee eee eeeee eeeee ee eee eeeeeee eeeeeeeee ee e eeeeeeeee eee eeeeeeeeeeeeeeeeee. Me eeeeeeee, (M)-8- eee (M)-8-eeeeeeeeeeeeee eeee eeeeeee eeeee-ee-eee eeeeeeeeeeeeeeeeee eeee eeeeeeeeee ee eeeeeeee.[‌88‌]

Meeeeeeeeeee Meeeeeeee

8-(8-Meeeeeeeeeee)-8-eeeeeeeeeeee (‌888‌, M8 = Me); Meeeeee Meeeeeeee:[‌88‌]

M eeee ee 8-eeeee-8-eeeeeeeeeeee (‌888‌; 888 ee, 8.88 eeee) ee MeMM (888 eM) eee eeeee ee M8MMMM (888 eM). Mee eeee eee eeeeeeeeeee ee e 888-eM eeeeee eeee, eeeeee eeee eeeee, eee eeeeeeeeee eee 88 eee ee 888 ee. Meeee eeeeeeeeee, M8M (888 eM) eee MeMe eeee eeeee, eee eee eeeeeee eee eeeeeeeee eeee MM8Me8; eeeee: 88–88%.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.
• 8.Meeeee-Meee, (8888) 8/8e, 888.