Synthesis and chemistry of tricarbonyl(7-norbornadienone)iron

Abstract

The synthesis, physical properties, and chemical reactivity of tricarbonyl(7-norbornadienone)iron are described.

C–C Bond-Forming and Bond-Breaking Processes from the Reaction of Diesters with Me3SnLi. Synthesis of Complex Bridged Polycycles and Dialkyl Aromatic Compounds

“…The minor compound was also isolated and identified as 9,10-dipropylanthracene ( 42c , 13% yield), which we suspect arises from a rearomatizing decarbonylation of 41c . The thermal decarbonylation of norbornadien-7-one derivatives to give aromatic compounds has been well documented . In general, the decarbonylation of these compounds is highly favored, since aromatization is the driving force of this transformation.…”

Dimethyl Sulphoxide a Useful Reagent for Organic Synthesis

“…This reagent also oxidizes allylic alcohols to the corresponding α, βunsaturated carbonyl compounds. The combination of DMSO with SO 3 / pyridine complex oxidizes tricarbonyl ( 7-norbornadienol) iron (9) to tricarbonyl (7-norbornadienone) iron (10) [31].…”

Methods in alkaloid synthesis. Imino ethers as donors in the Michael reaction

“…Purification by TLC using 1:1 pentaneether solvent gave two major products. The band of R/ 0.22 provided 85 mg (35%) of (Z)-3-(3'-mercaptopropylthio)acrylonitrile as a colorless oil: ir (CC14) 2218 cm-1; NMR (CC14) 7.02 (1 H, d, J = 10.5 Hz, C=CHCN), 5.22 (1 H, d, J = 10.5 Hz, C=CHS), 2.8 (4 H, m), 1.9 (2 H, m), 1.2 (1 H, t, J = 8 Hz, -SH); mass spectrum m/e (% rel intensity) 119 (100), 112 (38), 99 (12), 85 (17), 74 (29), 73 (12), 59 (14), 58 (14), 47 (27), 46 (39), 45 (55), 42 (10), 41 (71), 39 (22); mol wt (caled for C6H9NS2, of 50.1 g (0.212 mol) of 1,1 -diethoxy-3,3-trimethylenedithiopropane,22 60 ml of perchloric acid, and 100 ml of water in 400 ml of dioxane was stirred for 0.5 hr at room temperature. The reaction was extracted with 4 X 250 ml of ether, and the combined ether layers were washed with 6 X 200 ml of saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate.…”