Organolithiums are extremely good nucleophiles and strong bases, and it should not be a surprise that they readily react with epoxides, which are highly strained electrophiles. The nucleophilic attack of the organolithium opens the epoxide ring, forming an alkoxide ion, which, … Read more
Oseltamivir, sold under the brand name Tamiflu, is a widely used antiviral drug for the treatment and prevention of influenza. It belongs to a class of compounds known as neuraminidase inhibitors, which block the viral enzyme responsible for the release … Read more
In this article, we will summarize and compare the reactions of Grignard (RMgX), Gilman (R2CuLi), and organolithium (RLi) reagents. Let’s first see what unites and makes their properties similar or at least creates a pattern for us to predict the … Read more
In the previous post, we discussed ring expansion rearrangements where 4 and 5-membered rings were transformed into more stable, larger rings. Sometimes, the process goes in reverse direction, and larger rings are transformed into smaller rings. These are … Read more
Epoxides undergo ring-opening reactions under both acidic and basic conditions. Let’s clarify that by “basic conditions” we refer to a greater class of epoxide ring-openings when they are reacted with good nucleophiles. This includes a number of them such as … Read more
The reactivity of epoxides is due to the high ring strain of three-membered rings. The reactions of epoxides lead to the ring opening, forming an alcohol with a variety of other functional groups in the product. We have seen, in … Read more
Acid-Catalyzed Addition of Alcohols and Alkoxymercuration Alkenes can be converted to ethers by reacting them with alcohols in the presence of acid or using Hg(OAc)2 catalyst. You may wonder why use a toxic mercury catalyst if it … Read more
Ethers are named by both common and systematic nomenclature of the IUPAC rules. The common names are used for ethers with simple alkyl groups. To do this, we first identify the alkyl groups and arrange them in alphabetical order, followed … Read more
Ethers can be converted to alkyl halides when treated with HBr and HI in a sequence of two substitution reactions: This transformation represents two substitution reactions. First, the ether is converted into an alkyl halide and an alcohol, … Read more
Epoxides are three-membered rings containing an oxygen atom. They are associated with high ring strain, and this is the basis of their reactivity towards nucleophiles despite lacking a good leaving group. The ring strain is a combination of two destabilizing factors: angle … Read more
