Science of Synthesis

Pfeiffer, W. D., Science of Synthesis, (2007) 35, 424.

N-Bromosuccinimide reacts with hept-2-ene to afford 4-bromohept-2-ene (‌2‌), although the yield varies between 58 and 76% (‌Scheme 2‌).[‌10‌,‌11‌] In similar reactions a variety of products are possible; thus, octene yields both trans-1-bromooct-2-ene (‌3‌) and 3-bromooctene (‌4‌) in a ratio of 4.4:1 and in 65% overall yield. A 15% yield of dibrominated and higher brominated octanes are also obtained.[‌12‌] The reactions of dienes often lead to products by allylic rearrangement; for example, hexa-1,5-diene gives 1-bromohexa-2,5-diene as well as some 3-bromohexa-1,5-diene, whereas hexa-1,5-diene reacts with 2 equivalents of N-bromosuccinimide to give 1,6-dibromohexa-2,4-diene.[‌13‌,‌14‌]

‌Meeeee 8‌ Meeeeee Meeeeeeeeee ee Meeeee Meeeeee eeee M-Meeeeeeeeeeeeeee[‌88‌–‌88‌]

Meeeeeee ee eeeeeee eeeeee eee eeeeee eeee eee eeeeeeeee eeeeeeeeeee; eeee, eeeeeeeeeeeeeeeeeeee eeeeee eeee M-eeeeeeeeeeeeeeee ee eeee eee eeeeeeeee ‌8‌ ee eee eeeee eeeeeee (88%), eeeeeeee eeee eeeeeee eeeeeee ee eee eeeee eeeeeee eeeeeeee ‌8‌ eee ‌8‌ (88%) (‌Meeeee 8‌).[‌88‌] Meeeeeeee, eeeeeeeeeee eeeee eeeeee 8,8-eeeeeeeeeeeeeeeeee, eeeeeee 8-eeeeeeeeeeeeeeee ee eeee e eeeee eeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeee ee Meeeeeeeeeeeeeeeeeee[‌88‌]

Mee eeeeeeeeeee ee eeeeeeeeeeeeeeeeee eeee M-eeeeeeeeeeeeeeee eeeee e eeeeeee ee [8-(eeeeeeeeeee)eeeee]eeeeeee (88%) eee (8-eeeee-8-eeeeeeeeeee)eeeeeee (88%),[‌88‌] eeeeeee 8-eeeeeeeeeee-8-eeeeeeeeeeeee eeeee 8-[8-(eeeeeeeeeee)eeeee]-8-eeeeeeeeeeeee (88%) eee 8-(8-eeeee-8-eeeeeeeeeee)-8-eeeeeeeeeeeee (88%).[‌88‌] Meeeeeeeeeee eeeeeeeee eeeeeee (8-eeeeeeeee-8-eeee)eeeeeee (88%) eee (8-eeeeeeeee-8-eeee)eeeeeee (88%).[‌88‌,‌88‌] Meeeeeeeeee-8,8,8-eeeeee eee ee eeeeeee eeee M-eeeeeeeeeeeeeeee ee eeee e eeeeee eeeeeee, 8-eeeeeeeeeeeeeeee-8,8,8-eeeeee.[‌88‌] Meeeeeeee ee eeeeee eeeeeeeeeeee, eeee ee eeeeeeeeeeee, eeee M-eeeeeeeeeeeeeeee eee eeeeeee eeeeeeee eeeee ee e eeeeeee ee eee- eee eeeee-8,8-eeeeeeeeeeeeeeeeeeee (‌8‌).[‌88‌,‌88‌] Meeeeeeee, 8-eeeeeeeeeeeeeee-8-eee eeeeeee 8-eeeee-8-eeeeeeeeeeeeeee-8-eee,[‌88‌] eee 8-eeeeeeeeeeeeeeee (‌8‌) ee eeeeeeee eeee eeeeeeeeeee (‌Meeeee 8‌).[‌88‌–‌88‌] Meeeee eee eeee eeee eeeeeeee eeee eee eee eeeeeeeeee eeee eeeeeee eeeeeeeee eeeeeeee,[‌88‌] 8,8′-eeeeeeeeeeeeeeeeeeeeee,[‌88‌,‌88‌] eeeeeeeeeeee eeeeeeeeeeeee,[‌88‌] ee ee-eeee-eeeee eeeeeeee.[‌88‌]

‌Meeeee 8‌ Meeeeeeeeee ee Meeeeeeeeeee eeee M-Meeeeeeeeeeeeeee[‌88‌,‌88‌,‌88‌–‌88‌]

Mee eeeeeeee ee 8 eeeeeeeeeee ee M-eeeeeeeeeeeeeeee eeee 8 eeeeeeeeee ee eeeeeeeee-8,8-eeeee (‌88‌) eeeee eeee ee e eeeeeee ee 8,8-eeeeeeeeeeeeeeee-8,8-eeeee (‌88‌) eee eeeee-8,8-eeeeeeeeeeeeeeeeee (‌88‌).[‌88‌] Meeeeeeee-8,8-eeeee eeeeee eeee 8 eeeeeeeeee ee M-eeeeeeeeeeeeeeee ee 88°M ee eeee eee eeeeeeeeeee ‌88‌ eee eeee eeeeeeeee ‌88‌, ee eeee ee eeeeeee, eeee ee eeeeee ee eee eeeeeeeeeeeeeeeeee ee 8-eeeeeeeeeeeeee-8,8-eeeee (‌88‌) (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeeee ee Meeeeeeee-8,8-eeeee eeee M-Meeeeeeeeeeeeeee[‌88‌]

Mee eeeeeeee ee 8-eeeeeeeeeeeeee-8-eee eeee M-eeeeeeeeeeeeeeee eeeeeee 8-eeeee-8-eeeeeeeeeeeeee-8-eee, eeee e eeeee ee 8-eeeee-8-eeeeeeeeeeeeee-8-eee,[‌88‌] eeeeeee 8,8-eeeeeeeeeeeeeeee-8-eee eeeee 8-eeeee-8,8-eeeeeeeeeee-8-eee,[‌88‌] eee 8-eeeeeeeeeeeeee-8-eee eeeeee 8-eeeee-8-eeeeeeeeeeeeee-8-eee.[‌88‌] Me eeee eeee eeeeee eeeee eeeee eeeeee ee eeeeeeeeeee ee eee α-eeeeeeee ee eee eeeeeeee eeeeee eeee. M eeeeeeeee eeeee eeeeeeee ee e eeeeee eeee ee eeee eeeeeeee eeee e eeeeeeeee eeeee eeeeeeee ee e eeeeee eeee eee, ee eee eeee ee eee-8-ee-8-eee (‌88‌), 8-eeeeeeee-8-ee-8-eee (‌88‌) ee eeeeeeee ee 88% eeeee, eeeeeeee eeee 8-eeeeeeee-8-ee-8-eee (‌88‌, 8%), eeeee ee eeeeeee ee eeeee ee ee eeeeeee eeeeeeeeeeeee ee 8-eeeeeeee-8-ee-8-eee. 8-Meeeeeeee-8-ee-8-eee (‌88‌) eee 8-eeeeeeeee-8-ee-8-eee (‌88‌) (eeeee 88:8) eee eeeeeeeee eeeeeeee eeee eeee-8-ee-8-eee (‌88‌) (‌Meeeee 8‌).[‌88‌]

‌Meeeee 8‌ Meeeeee Meeeeeeeeee ee Meeeeeeeee Meeeeeeeeeee[‌88‌]

Meeeeeeeeeee Meeeeeeee

(M)-8-Meeeeeeee-8-eee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee eeee eeeeeeee ee eeeeeee eee eee eeeeeee eeeeeeeeeeeee eeee eee.

Meee-8-eee (88 e, 8.88 eee), MMM (88.8 e, 8.88 eeee), MMMM (8.8 e), eee MMe8 (888 eM) (MMMMMMM: eeeee) eeee eeeeee ee e eeeee-eeeeee eeeee (888-eM eeeeeeee) eeeeee eeee e eeeeeee, eeeeee eeeeeeeee, eee M8 eeeee eeee. Mee eeeeeee eee eeeeeee eee eeeeeeee eeeee M8 eee 8 e, eeeeee eeeee eeeeee, eee eee eeeeeeeeeee eeee eee eeeeee eee eeeeeee ee eeeeeeeeee. Meee eeeee eeeeeeee eee eeeeee eeee MMe8 (8 × 88 eM) eee eee eeeeeeee eeee eeeee ee eee eeeeeeee. Mee MMe8 eee eeeeeee eeee eee eeeeeeee ee eeeeeeeeeeee eeeee eeeeeee eeeeeeee eeeeeee e eeeeee (88 ee) eeeeee eeee eeeee eeeeeee. Mee eeeeeee eee eeee eeeeeeeee eeeee eeeeeee eeeeeeee eeeee e Meeeeee eeeee. Meee eeeeeeeeeeeee eeee eeeeeee eee eeeee M8; eeeee: 88.8 e (88%); ee 88.8–88°M/88 Meee; e88M 8.8888.

eeeee-8-Meeeeeee-8-eee (‌8‌) eee 8-Meeeeeee-8-eee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee eeee eeeeeeee ee eeeeeee eee eee eeeeeee eeeeeeeeeeeee eeee eee.

Meeeee (88 e, 8.88 eee), MMM (88.8 e, 8.88 eee), MMMM (88 ee, 8.88 eeee), eee MMe8 (888 eM) (MMMMMMM: eeeee) eeee eeeeeeee eeeee M8. Mee eeeeeeee eee eeeeeeee ee eeeee 8 e. Mee eeeeeee eee eeeeee eee eee eeeeeeeeeee (88.8 e) eeee eee eeeeeeeee eee eeeeeeeee ee eeeeeee eeeeeeeeee. Me eee eeeeee eeeeeee eeeee eeee eeeee eeeeeeee ee eeee MMe8 eee eeeee. Mee eeeeeeee eeee eeeeeeee eeee eee eeeeeeee eeee eeeee eee eeeeeee eee eeee ee eee eeeeeeeee eeeeee eeee eeeeeee ee eeeeeeeeeeee ee eeeeeee eeeeeeee (88 Meee). Mee eeeeeee eee eeeeeeeee ee 88°M/8.88 Meee eee eee eeeeeeeeee, eeeeeeeeee eeeeee ee eeeeeeeeeeeeee eeeeeeee, eee eeeeeeeee ee e eeee eeee (−88°M). Mee eeeeeeeeee (88.8 e) eee eeeeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeee (8 Meee) eeeeeee e Me eeeeee eeeeee (88 ee) ee eeee eeeeeeeee eeeeeeeeee eee eeeee eeeeeeeee: eeeee-8-eeeeeeee-8-eee; eeeee: 88 e (88%); ee 88–88°M/8 Meee; eee 8-eeeeeeee-8-eee; eeeee: 8.8 e (88%); ee 88–88°M/88 Meee. Meee eeeeeeeeeeee eee eeeeee eeeeeeeeee eeeeeee eeee eeee eeeeeeee ee ee. 88% eeeee.

eee eee eeeee-8,8-Meeeeeeeeeeeeeee-8-eee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

MMMMMMM: Meeeeeeee eeeeeeee ee ee eee, eeee, eee eeeeeeeeeee eeeee eeeeeeee eeee eeeeeeee ee eeeeeee eee eee eeeeeee eeeeeeeeeeeee eeee eee.

M eeeeeee ee eeeeeeeeeeee (88.8 e 8.88 eeee), MMM (888.8 e, 8.88 eee), eee MMMM (8 e, 8.88 eeee) ee MMe8 (888 eM) (MMMMMMM: eeeee) eee eeeeeeee eee 8 e, eeeeee eeee eee, eee eeeeeeee ee eeeeee eeeeeeeeeee. Mee eeeeeeee eee eeeeee eeee M8M, eeeee (MeMM8), eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Mee eeeeeee eee eeeeeeeee eeeeeee ee eeeeee. Meeee eeeee ee eee- eee eeeee-8,8-eeeeeeeeeeeeeeee-8-eeee: 88 e (88%). Mee eeeeeee ee eeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eeeeeeeeeeee eeeee e Meeeeee eeeeee: eee-eeeeee; ee 88–88°M/8 Meee; eeeee-eeeeee; ee 88°M/8 Meee.

8-Meeeeeeeeeeeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

M eeeeeee ee MMM (88.8 e, 88 eee) eee eeeeeeeeeee (88.8 e, 8.88 eee) [eeeee ee eeeeeeeeee eeeeeeeee ee eeeeeee eeeeeeeeeeee eeeeeeeeeeeee (8.88 eee·M−8)] eee eeeee eeeeeee (MMMMMMM: eeeeeeeeee) eee eeeeee eeee eeeeeeee eee 88 eee. Meeee eeeeeee eee eeeeeee ee eee eeeeeeeeeee eeee eee eeeeee ee eeeeeeeeee, eee eeeeeeee eee eeeeeeeeeeee eeeeeeeee eeeee eeeeeee eeeeeeee; eeeee: 88 e (88%); ee 88–88°M/8 Meee.

References

Meeeeee Meeeeeeeeee

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