TY - JOUR
T1 - Preparation of Functionalized trans-Perhydroindans from Substituted Benzoic Acids
T2 - Reductive Alkylation-Halolactonization-Free Radical Cyclization
AU - Chuang, Che Ping
AU - Gallucci, Judith C.
AU - Hart, David J.
PY - 1988/6/1
Y1 - 1988/6/1
N2 - Reductive alkylation of m-toluic acid (7), m-anisic acid (8), benzoic acid (9), and 2,3-dimethylbenzoic acid (31) with selected alkyl halides followed by iodolactonization and side-chain modification gave free radical precursors 13, 14, 19, 27, and 34. Treatment of 13, 14, and 19 with tri-n-butyltin hydride and AIBN gave mixtures of perhydroindans and perhydronaphthalenes. Similar treatment of 27 and 34 gave trans-perhydroindans 28 and 35, respectively, as the major products. Iodo lactone 47 was also prepared from ethyl m-iodobenzoate (38) and converted to angularly oxygenated perhydroindans 48 and 49 by using a free radical cyclization.
AB - Reductive alkylation of m-toluic acid (7), m-anisic acid (8), benzoic acid (9), and 2,3-dimethylbenzoic acid (31) with selected alkyl halides followed by iodolactonization and side-chain modification gave free radical precursors 13, 14, 19, 27, and 34. Treatment of 13, 14, and 19 with tri-n-butyltin hydride and AIBN gave mixtures of perhydroindans and perhydronaphthalenes. Similar treatment of 27 and 34 gave trans-perhydroindans 28 and 35, respectively, as the major products. Iodo lactone 47 was also prepared from ethyl m-iodobenzoate (38) and converted to angularly oxygenated perhydroindans 48 and 49 by using a free radical cyclization.
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U2 - 10.1021/jo00249a014
DO - 10.1021/jo00249a014
M3 - Article
AN - SCOPUS:0001062836
SN - 0022-3263
VL - 53
SP - 3210
EP - 3218
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 14
ER -