Regioselectivity in the reductive cleavage of syn-and anti-2-methylspiro [cyclopropane-1, 1'-indene]. Elucidation of the role of steric effects

SW Staley, MA Fox, TK Hirzel

Index: Staley,S.W. et al. Journal of the American Chemical Society, 1976 , vol. 98, # 13 p. 3910 - 3916

Full Text: HTML

Citation Number: 5

Abstract

Abstract: The title compounds (11 and 12, respectively) have been shown to suffer reductive cleavage at essentially the same rate on treatment with lithium or sodium in liquid ammonia at ca.-33 OC. Six cyclopropyl ring-opened products have been identified as products of this reaction. The regioselectivity [opening of bond a relative to bond b (ka/kb)] is 4 for 11 and 0.6 for 12 (in lithium-liquid ammonia). These opposite regioselectivites are explained in part ...

Related Articles:

Catalytic Dehydrogenation of Hydroaromatic Compounds with Benzene1

[Adkins; Richards; Davis Journal of the American Chemical Society, 1941 , vol. 63, p. 1320,1322]

Synthesis and thermal rearrangement of 7-(1, 2-butadien-1-yl) bicyclo [2.2. 1] hept-2-ene [7-(3-methylallenyl) norbornene]

[Duncan, James A.; Bohle, D. Scott; Blanchard, Charles A.; Bosse, Mark L.; Noland, Terry W.; et al. Journal of the American Chemical Society, 1982 , vol. 104, # 10 p. 2837 - 2839]

Synthesis of biological markers in fossil fuels. 2. Synthesis and carbon-13 NMR studies of substituted indans and tetralins

[Adamczyk, Maciej; Watt, David S.; Netzel, Daniel A. Journal of Organic Chemistry, 1984 , vol. 49, # 22 p. 4226 - 4237]

Radical pathways of coal dissolution in hydrogen donor media. 2.. beta. Scission and 1, 2 aryl migration reactions of radicals derived from methylindans and tetralin at …

[Franz, James A.; Camaioni, Donald M. Journal of Organic Chemistry, 1980 , vol. 45, # 26 p. 5247 - 5255]

Cyclization-rearrangement of alkylstyrenes. 1. A. 1-Phenyl-1-pentene and homologs. B. A short synthesis of calamenene

[Condon, Francis E.; West, David L. Journal of Organic Chemistry, 1980 , vol. 45, p. 2006 - 2009]

More Articles...