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You are using Science Of Synthesis as a Guest. Please login or sign up for a free trial to access the full content. Variation 4: SN2 Displacement of Activated Aryl Halides by Hydroperoxides

DOI: 10.1055/sos-SD-031-00501

Chen, J.; Chiu, C. K.-F.Science of Synthesis, (200731668.

Activated hetaryl halides such as chloropyrimidine and chlorotriazine can be substituted readily by the tert-butyl peroxide anion to provide the corresponding pyrimidinyl[‌11‌,‌12‌] and triazinyl[‌5‌,‌13‌] peroxides.

Me eeeeeeee eee eeeeeeeeeeeee eeeeeeeeeeeeeeeeeeeee 88 ee eeeeeeeeeeeeeeeeeee 88 ee 88 eeee eeee-eeeee eeeeeeeeeeeee ee eee eeeeeeee ee e eeee (MeM), e eeeeeee ee eeeeeeeeeeeeeeeeeeeee 88 (Meeeee 8) eee eeeeeeeeeeeeeeeeeee 88 eee 88 (Meeeee 8) eeee eeee eeeeeeee ee eeee eeeeee (8888%).

Meeeee 8 Meeeeeeee ee Meeeeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8

M8 M8 Meeeeeeeee Meeee (%) Mee
MMe M 8888°M, 8.8e 88 [‌88‌]
Me MM8Me 88°M, 8.8e 88 [‌88‌]
Me MM8Me 8888°M, 8.8e 88 [‌88‌]
MMe MM8Me 8°M, 8.8e 88 [‌88‌]
Me MM 8888°M, 88.8e 88 [‌88‌]

Meeeee 8 Meeeeeeee ee Meeeeeeeeeeeeeeeeee[‌88‌]

Meeeeeeeeee 8M

M8 M8 Meeeeeeeee Meeee (%) Mee
Me M 88°M, 8.8e 88 [‌88‌]
M MM8 8°M, 8.8e 88 [‌88‌]
Me MM8 88°M, 8.8e 88 [‌88‌]

Meeeeeeeeee 8M

M8 M8 Meeeeeeeee Meeee (%) Mee
Me Me 88°M, 8.8e 88 [‌88‌]
Me MM8 88°M, 8.8e 88 [‌88‌]
Me MM 88°M, 8.8e 88 [‌88‌]
8-Mee MM 88°M, 8.8e 88 [‌88‌]
8-MeM8M8 MM 88°M, 8.8e 88 [‌88‌]

M eeeeee ee eeee-, ee-, eee eeeeeeeeeeeeeeeeee, 88, 88, eee 88, eeeeeeeeeeee, eeee eeee eeeeeeeeeeee eeeeeeee ee eeeeeeee ee eee eeeeeeeeeeeee eeeeeeeeeeeeeee eee eeee-eeeee eeeeeeeeeeeee ee eee eeeeeeee ee e eeee (MeM, MeMM), eee eeeeeeee ee eeeeeeeeeee eeeeee (Meeeee 8). Meeeeee, eeeeeee eeeeeee eeeeee ee eeeeeeeee ee eee eeeeeeee ee eeeee eeeeee eeeeeeeee eeeeeee ee eeeee eeeeeeeeeee eeeeeeeee eeeeee. Mee eeeeeeeeeeeeeeeee 88 eeeeeeeeee eeeeeeeee ee eeeeeee eeeee eeeeeeeeeeeeeeeeee 88 eeeeeeee eeeeee eeeeeeeeeeee.[‌8‌]

Meeeee 8 Meeeeeeeeee ee Meeeeeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

8,8,8-Meee(eeee-eeeeeeeeeee)-8,8,8-eeeeeeee (88); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeeeeeeee eee eeeeeeeee eee eeeee ee eeeeeeeee eeeeeeeeeee. Meeeee eeeeee eeeeeeeeeee eeeeee ee eeeee eeeeee eeeeeeeee, eeeeeee, eee eeeeeeee.

M eeeeeeeeee ee MeM (8.8e) ee eeeeeeeee eeeee (88eM) eee eeeeeee ee eeeeeeee eeeeeeee ee e eeee ee e-MeMMM (8.8e, 88.8eeee) ee eeeeeeeee eeeee (88eM) ee 8°M. Mee eeeeeeeee eeeeeee eee eeeeeee ee ee eee eeeeeee eeee e eeeeeee ee e-MeMMM (8.88e, 88.8eeee) eee 8,8,8-eeeeeeeee-8,8,8-eeeeeeee (8.8e, 88eeee) ee eeeeeeeee eeeee (88eM). Mee eeeeeee eee eeeeeee eee 8e, eeee eeeeeeee, eee eee eeeeeeee eee eeeeeeeeeeee. Mee eeeeeeeee eeeeeee eee eeeeeeeee ee MM8Me8, eeeeeee eeee eeeeeeeee eeeee, eee eeeeee ee e eeeeeeeeeeee ee eeeeee eeeeeeeeeeeeeee; eeeee: 88.8%; ee 8888°M.