22592-16-1Relevant academic research and scientific papers
Implication of a Common Trimethylenemethane Intermediate in Dimer Formation and Structural Methylenecyclopropane Rearrangement of a Bicyclohex-1-ene to a 5-alkylidenebicyclopentane
Salinaro, Richard F.,Berson, Jerome A.
, p. 2228 - 2232 (1982)
Stereospecifically labelled 2,6,6-trimethylbicyclohex-1-ene (17b), generated by α-elimination from 1,1-dibromo-6-trans-trideuteriomethylhepta-1,5-diene (8b), dimerizes to stereospecifically labelled and products, 15b and 16b, and to
Ring-Enlarging Annulatons. A One-Step Conversion of Cyclic Silyl Acyloins and ω-Alkynyl Acetals to Polycyclic Enediones
Balog, Aaron,Curran, Dennis P.
, p. 337 - 344 (2007/10/02)
A new sequence of cationic reactions that converts cyclic silyl acyloins and ω-alkynyl acetals to polycyclic enediones is reported.For example, treatment of bis-1,2-((trimethylsilyl)oxy)cyclobutene and 2-(ethylenedioxy)-5-heptyne with excess boron trifluoride etherate in methylene chloride for 2 days provides 4-acetyl-3,5,6,6a-tetrahydro-6a-methyl-1-(2H)-pentalenone in 58percent yield.This product is formed via a sequence involving a Mukaiyama aldol reaction, a pinacol ring expansion, and a 5-exo-dig alkynyl ketone cyclization.In the case of terminal alkynes, the last cyclization occurs in a 6-endo-dig fashion.The scope and limitations of this process are studied, and a number of bi- and tricyclic ring systems are formed.
Direct Conversion of Terpenylalkanolamines to Ethylidyne N-Nitroso Compounds
Abidi, S. L.
, p. 2687 - 2694 (2007/10/02)
A series of mono- and diterpenylalkanolamines bearing isopropylidene functionality on the terpene group was reacted with sodium nitrite in aqueous acetic acid to yield ethylidyne N-nitroso analogues.The key feature of this direct conversion involved initial N-nitrosation followed by apparent elimination of a "CH4" unit (not necessarily methane) from the isopropylidene double bond.The product distribution data for ethylidyne nitrosamines derived from tertiary terpenyl alkanolamines reflect the conformational outcome of the nitrosative dealkylation process.For β,γ-unsaturated allylic diterpenylethanolamines, electronic effects appeared to be important for controlling the product distribution of ethylidyne nitrosamines in light of the highly selective α-cleavage observed in the nitrosation reactions.
Synthesis of (+/-)-Actinidine by an Intramolecular Cycloaddition Process
Davies, Lyn B.,Greenberg, Sydney G.,Sammes, Peter G.
, p. 1909 - 1912 (2007/10/02)
A new synthesis of (+/-)-actinidine (1), which relies on intramolecular cycloaddition of an acetylene across a pyrimidine ring, is described.Preparation of 5-(hept-5-yn-2-yl)-4,6-dihydroxypyrimidine (2) followed by thermolysis afforded 1-hydroxyactinidine
