Free radical addition of 2-bromoalkanoic acids to alkenes

T Nakano, M Kayama, Y Nagai

Index: Nakano, Taichi; Kayama, Mikio; Nagai, Yoichiro Bulletin of the Chemical Society of Japan, 1987 , vol. 60, # 3 p. 1049 - 1052

Full Text: HTML

Citation Number: 9

Abstract

The benzoyl peroxide-catalyzed reaction of 2-bromoalkanoic acids such as bromoacetic, 2- bromopropionic, and 2-bromobutyric acid with 1-alkenes was found to proceed through the addition of the C–Br bond across the double bond followed by cyclization affording 4- alkanolides in good yields.

Related Articles:

A selective and efficient method for alcohol oxidations mediated by N-oxoammonium salts in combination with sodium bromite

[Inokuchi, Tsutomo; Matsumoto, Sigeaki; Nishiyama, Tokio; Torii, Sigeru Journal of Organic Chemistry, 1990 , vol. 55, # 2 p. 462 - 466]

Substituent directed oxidative cyclization with cetyltrimethylammonium permanganate: A general approach to the synthesis of γ-and δ-lactones

[Rathore, Rajendra; Vankar, Padma S.; Chandrasekaran, S. Tetrahedron Letters, 1986 , vol. 27, # 34 p. 4079 - 4082]

Synthesis of γ-lactones and unsaturated bis γ-lactones via Cu–Fe-mediated reductive cyclization of di-and tri-α-halogenated carboxylic esters

[Somech, Iris; Shvo, Youval Journal of Organometallic Chemistry, 2000 , vol. 601, # 1 p. 153 - 159]

Synthesis of lactones by Baeyer-Villiger oxidation with magnesium monoperphthalate hexahydrate

[Mino, Takashi; Masuda, Satoshi; Nishio, Masayuki; Yamashita, Masakazu Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2633 - 2635]

IBX/n-Bu 4 NBr/CH 2 Cl 2–H 2 O: a new mild system for selective oxidation of secondary alcohols

[Tetrahedron, , vol. 61, # 38 p. 8995 - 9000]

More Articles...