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35.2.4.1.2.1 Variation 1: Reactions with Aliphatic and Alicyclic Alkenes

DOI: 10.1055/sos-SD-035-00418

Pfeiffer, W. D.Science of Synthesis, (200735424.

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]

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

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