Science of Synthesis

Smalley, R. K., Science of Synthesis, (2002) 11, 374.

Modifications of substituents on the 2,1-benzisoxazole ring are relatively few, primarily because of the fragility of the ring system under oxidizing, reducing, thermal, photolytic, and strongly basic conditions.

Me eeeeeeee ee eee 8-eeeeeee eeeeeeeeee (Meeeeee ‌88.88.8.8.8.8‌), 8-eeeeee-8,8-eeeeeeeeeeeee[‌888‌] eee eee 8- eee 8-eeeeeee eeeeeeeeeee[‌888‌] eeeeeeeee eeeeeee ee eee eeeeee eeeee eeee M-eeeeeeeeeeeeeeee, ee ee 8-eeeeee- (‌888‌) eee 8-eeeeee-8,8-eeeeeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeeeeeee eeeeeeeeeee, e.e. ‌888‌, eeeee eee eeeeee eeeeeeeeeeee, eeeeee ee eeeeeee eeeeeeee eeeeeee eee eeeeeee eeeeeeeeeeee eeeeeeeeeeee ee eeeeeee eeee e eeeeeee ee eeeeeeee, e.e. eeeeeee eee eeeeeeeeeee.[‌888‌,‌888‌] Mee eeeeeee eee ee eee eee eeeeeeeee ee 8,8-eeeeeeeeeeeeeeeeeeeeeeeeee, e.e. ‌888‌, ee eee Meöeeee eeeeeeee eeeeeeeee[‌888‌,‌888‌] (‌Meeeee 88‌). Mee eeeeeeee eeeee eeee 8-(eeeeeeeeeee)-8,8-eeeeeeeeeeeee (‌888‌) eee ee eeee eeee eee eeeeeeee ‌888‌ ee eeeeeeee ee eeeeeeeee ee eee eeeeeeeee eeeee ‌888‌ eeee eeeeee eeeeeeee eeeeeeeee ee eee eeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌888‌] Meeeeeeeeeee eeeeeeeee ee eee eeeeeeeeeeeee ee eee eeeeeee eeeeeeee eeeeeee eeeeeeee ee eee eeeeeeeee eeee eee eeee eeeeeeee eeeee eeeeee eeeeeeeeeee.[‌888‌,‌888‌] Meeeeeeee ee eeeee-8,8-eeeeeeeeeeeeee ee eee eeeee eeeeeeeee eeeeeee eeeeeee eeeeeeeee eeee-eeeeeeee ee e 8-eeeeeeeee eeeeee ee eeeeeeeee eee eee eeee eeeeeeee ee eee eeeeeeeee eeee eeee eee eeeeee eeee[‌888‌] eee eeee eee(MM) eeeeeeee eee eeeeeeeeeeee eeeeeeeeeeee eeee.[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-(Meeeeeeeeee)-8,8-eeeeeeeeeeeee eee 8,8-Meeeeeeeeeeee- 8-eeeeeeeeeeee[‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8,8-Meeeeeeeeeeee-8-eeeeeeeeeeee[‌888‌]

Meee eeeeeeeee, e.e. ‌888‌, eeeeeeee ee eee eeeeeeeeeee eeeeee eeee eee eeeeeeeeee eeee eee eeeeeee eeeeeeee ee eeeeee eeeeeeee, eeeeeeeeeee ee eee Meeeeee–Meeeee eeeeeeeee ee eeeeeee ee eeeee eeeeeee eeeeeeeeeee, e.e. ‌888‌ (‌Meeeee 88‌).[‌8‌,‌888‌]

‌Meeeee 88‌ Meeeeeeee ee 8-Meeeeee-8,8-eeeeeeeeeeeee eeee 8,8-Meeeeeeeeeeee-8-eeeeeeee Meeeeeee[‌8‌]

Meeeeeeee eeeeeeee ee eee 8-eeeeee eeeee eee eeee eeeeeeee eee 8-eeeeee-8,8-eeeeeeeeeeeeee eeee eeeeee eeeeeeeee ee eeeeeeeee eeeee,[‌888‌] eee eee 8-eeeeee eeeee ee 8-eeeeee-8,8-eeeeeeeeeeeee ee eeeeeeeeeeee eeeeeeee ee eeee ee eeeee eeee eeeeeee eeee.[‌888‌] Me eeeeeeee, eeeeeeee eeeeeeeeee ee eee 8-eeeeee eeeee ee eeeeeee eeee 8,8-eeeeeeee-8,8-eeeeeeeeeeeeeee eeeee, e.e. ‌888‌, eee eeeeeeeeeeeee ee eeeeeeee ‌888‌ eee ‌888‌ ee eee eeeeeeeee ‌888‌ eeeeeeee eeee eee 8-eeeeeeeee eeeee ee eee eeeeeeee ee e eeeeeeeeee eeeeeee eee e eeeee eeeee eeeeee eee eeeee eeeeee eeeeeee eeeeeeeeeeee eeeeeeeeeeee eeeeeeeee (‌Meeeee 88‌).[‌88‌] Me eeee, eee eeeeeeeeeee eeee ‌888‌ eeeeeeeee eeeeeeeeeeee eeee eeee eeeeeeeee ee eee eeeeeee ee eeee, eee eeeeeeee eeee eeeeeeeeeeeeee eeeee ee eeee 8-(β-eeeeee) eeeeeeeeeee eee 8-eeeeeeeeee, eeeeeeeeeeee.[‌88‌]

‌Meeeee 88‌ Meeeeeeee Meeeeeeeeeeee ee eee 8,8-Meeeeeee-8,8-eeeeeeeeeeeeeee Meeeeeeee[‌88‌]

Mee eeeeeeeeee, eee ee eee eeeeee eeeeeeee, eeeeee ee eee eeeeeeeee ee 8,8-eeeeeeee-8,8-eeeeeeeeeeeeeee eeeee, e.e. ‌888‌, ee eeeee eeeeeeeeeeeeeee ee e eeeeeeeeeee ee eee 8-eeeeee eeeee eee ee ee eeeeeeeeeeee ee eee 8-eeeeeeee. Meee eeeeeee ee eeeeeeee ee eee eeeeeeee ee eee eeeeeeeeeee eeee ‌888‌ eeee 8-eeeeeeeeeeeeeeeeee-8-eeeeeeeeeeee, ee eeeee eee eeeeeeeee eeeeee eeeeee eeeeeeeeee ‌888‌, ee eeee eeeeeeee, eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeee ‌888‌ eee eeeeee ee eee eeeeeee eeeee ee eee 8-eeeeeeee ee eee 8,8-eeeeeeeeeeeee eeee (‌Meeeee 88‌).[‌88‌]

‌Meeeee 88‌ Meee Meeeeee ee e 8-Meeeee-8,8-eeeeeeeeeeeeeee Meee ee e Meeeeeeeeee-8,8-eeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeeee

8-(Meeeeeeeeee)-8,8-eeeeeeeeeeeee (‌888‌):[‌888‌]

Me e eeee ee 8-eeeeee-8,8-eeeeeeeeeeeee (‌888‌; 8.88 e, 88 eeee) ee MMe8 (888 eM) eee eeeee MMM (8.88 e, 88.8 eeee) eee eeeeeeeee eeeeeeee (888 ee). Mee eeeeeee eee eeeeee eeeee eeeeee eee 88 e eeeee eeeeeeeeeee ee e 888-M eeeeeee. Mee eeeeeee eee eeeeee, eeeeeeee, eee eee eeeeeeee eee eeeeeeeeeeee ee eeee e eeee eee (8.8 e) eeeee eee eeeeeeeee eeee eee eeeeee (888 eM). Mee eeeeee eeeeeee eee eeeeeeeeee eeee ee 888 eM eee eeee eeeeee ee eeee eee eeeeeeeeeee eeeeeee; eeeee: 8.88 e (88%); ee 88–88.8°M.

8,8-Meeeeeeeeeeee-8-eeeeeeeeeeee (‌888‌):[‌888‌]

Me e eeee ee 8-(eeeeeeeeeee)-8,8-eeeeeeeeeeeee (‌888‌; 8.88 e, 88.8 eeee) ee Me8M (88 eM), eeeee M8, eee eeeee eeeeeeee (8.88 e, 88.8 eeee) eee eee eeeeeee eee eeee eeeeeee eeeeeeeee. Mee eeeeeeeee eeeeeeeeeee ee eee eeeeeeeeee eeeeeee eee eeeeeeee eee, eeeeee eeee Me8M, eee eeeee; eeeee: 8.88 e (88%); ee 888–888°M.

M eeee ee 8 M MeMM (88.8 eM, 88.8 eeee) eee eeeee ee e eeeeeeeeee ee eee eeeeeeeeee eeeeeee (8.88 e, 88.8 eeee) eee 8-(eeeeeeeeeeeee)-8-eeeeeeeeeeeeee (8.88 e, 88.8 eeee) ee 88% MeMM (88 eM) eee eee eeeeeee eee eeeeeee eeeeeeeee. M eeee ee 8 M MMe (88 eM) eee eeee eeeee eee, eeeee eeeeeeee eee 8.8 e, eee eeeeeeeee eee eeee eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee Me8M eeeeeeee eeee eeeeee eeeeeeeeeeee eeee eee ee MeMMM8, M8M, eee ee MeMe, eeee eeeee eee eeeeeeeeeeee ee eeee eee eeeee eeeeeee ee ee eeeeee eeeee (8.8 e). Meee eeeeeee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee 888–888 eeee, MMMe8) eeeeeeee ee eeeeeeeeeeeeeee (8-eeeeeeeeeeee); eeeee: 8.88 e (88%); ee 888–888°M.

8,8-Meeeeeeeeeeee-8-eeeeeeeeeeee (‌888‌):[‌888‌]

M eeee ee eee 8-(eeeeeeeeeee) eeeeeeee ‌888‌ (8.88 e, 8 eeee) ee MeMM (8 eM) eee eeeee ee e eeeeeeeeee ee eee eeeeee eeee ee MeMM (8.88 e, 88.8 eeee) ee MeMM (88 eM) eeeeee ee ee eee eeee ee eee eeee. Mee eeeeeee eee eeeeeee, eee eeeeeee ee eeeee ee eeeeeeeee, eeee eeeeee eeee eee eeeee (88 eM) eee eeeeeeeee eeee Me8M (8 × 88 eM). Mee Me8M eeeeeeee eeee eeeeeeee, eeeeee eeee ee MeMe, eeeee, eee eeeeeeeeeeee ee eeee eee eeeeeeeeeee eeeeeeeeee ‌888‌; eeeee: 8.88 e (88%); ee 888–888.8°M.

Mee eeeeeeeeeee eeeeeeeeee (8.88 e, 8.8 eeee) eee eeeee ee e eeeeeeeeee ee MeMMM8 (8.8 e, 88 eeee) ee MMMM (88 eM) eeeeeeeeee ee 888°M eee eeeeeee eeeee e eeeeee ee M8 eee eeeeeee. Mee eeeeeee eee eeeeee eee 8 eee, eeee eeeeee eeeeeee ee ee, eeeeeeeee ee M8M, eee eeeeeeeee eeee Me8M (8 × 888 eM). Mee eeeeeeee Me8M eeeeeeee eeee eeeeee eeee M8M (8 × 88 eM), eee ee MeMe (8 × 88 eM), eeeee, eee eeeeeeeeeeee ee eeee e eeeeee eee (8.88 e). Mee eee eee eeeeeeee ee eeeee eeeeeeeeeeeeee (eeeeee eee, 8% MeMM/MMMe8) ee eeee e eeeee eeeeeee (8.88 e) eeeee eee eeeeeeeeeeeeee (MeMe/eeeeee); eeeee: 8.88 e (88%); ee 88–88°M.

8-(Meeeeeeeeeeee)-8-eeeeee-8,8-eeeeeeeeeeeee:[‌88‌]

M eeee ee 8-eeeeee-8,8-eeeeeeeeeeeee-8-eeeeeeeeeeee (8 e, 88 eeee) ee MeMM (888 eM) eee eeeee eeeeee ee e eeee ee MeMM8 (8.88 e, 88 eeee) eee MeMM (8.8 e, 88 eeee) ee MeMM (88 eM). Mee eeeeeee eee eeeeeee ee ee eee 8 e eee eeee eeeeeeee ee eee eeeeeeee eeeeeeee ee 88% ee MMe (88 eM, 88 eeee). Mee MeMM eee eeeeeee ee eeeeeeeeeee, eee eee eeeeeee eee eeeeeeeee ee MM8Me8, eee eeeeeeeee eeee M8M. Mee eeeeeee eeeee eee eeee eeeee (MeMM8) eee eee eeeeeee eeeeeee ee eeee eee eeeeeee; eeeee: 8.8 e (88%); ee 888–888°M.

8-Meeeeee-8,8-eeeeeeeeeeeee (‌888‌):[‌8‌]

M eeee ee 8,8-eeeeeeeeeeeee-8-eeeeeeeeee eeee (8.88 e, 8.88 eeee) eee eeeeee eeeeeeee (8 eM) ee eee eeeeeee (88 eM) eee eeeeee eeeee eeeeee eee 88 e. Mee eeee eee eeee eeeeeeeeeeee ee 88 eM ee eeeeeeeeeeee eee eeeeeee (88 eM) eee eeeee eee eee eeee eee eeeee eeeeeeeeeeee ee 88 eM. Me eee eeeeeeee eeee eee eeeee eeeeeeeeeee ee ee, eeee 8 eee, MeMe8 (8.88 e, 88.8 eeee). Mee eeeeeee eee eeeeeee ee 88°M eee 8.8 e eee eeee eeeeee eeeee eeeeee eee 8.8 e. Me eee eee-eeeeee eeeeeee eee eeee eeeee eeeeeeee 88% MM (88 eM), eeeee eeeee eee eeeeeee eee eeeeeeeee eeee eeeeeee. Mee eeeeeee eeeeeee eee eeeeee eeeeeeeeeeee eeee M8M, 88% ee MeMMM8, eee M8M. Meeeeeeeeee ee eee eeeee (MeMM8) eeeeeee eeeeeee eeee eee eeeeeee ee e eeeeeeeee eeeeee; eeeee: 8.8 e (88%); eeee eee eeeeeeeeeeee eeee ee MeMM ee eeeeeee; eeeee: 8.88 e (88%); ee 88–88°M.

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) M 8e, 888.