Direct conversion of ethers to esters by trichloroisocyanuric acid

Juenge, Eric C.; Beal, David A.

doi:10.1016/s0040-4039(00)76360-x

Cited by 26 publications

(8 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Common functional groups such as esters (entries 1 and 3), lactones (entries 7 and 8), double bonds (entries 6 and 10), and TBS (entry 5) survived the TCCA conditions. Moreover, the N -debenzylation and N -chlorination reaction rate was observed to be faster than the O -debenzylation rate (entry 4) and the hydroxyl oxidation rate (entry 8 and for 22 → 24 and 23 → 25 ). , N -Monobenzylated substrates afforded the N -debenzylated and N -chlorinated compounds as the major products (entries 9 and 13). When N -benzyl was substituted with N -allyl or N -alkyl, N -deallylated or N -dealkylated compounds were the major products (entries 10 and 11).…”

Section: Resultsmentioning

confidence: 93%

Enantiospecific Total Synthesis of (+)-Tanikolide via a Key [2,3]-Meisenheimer Rearrangement with an Allylic Amine N-Oxide-Directed Epoxidation and a One-Pot Trichloroisocyanuric Acid N-Debenzylation and N-Chlorination

et al. 2013

View full text Add to dashboard Cite

The enantiospecific total synthesis of the δ-lactonic marine natural product (+)-tanikolide (1), isolated from Lyngbya majuscula , was achieved using a [2,3]-Meisenheimer rearrangement as the key reaction. During this rearrangement, we discovered that the allylic amine N-oxide could direct the m-CPBA double-bond epoxidation to the syn position. The resulting syn product 8 underwent epoxide ring opening under the m-CBA conditions to give the five- and six-membered cyclic ether amine N-oxides, which we further treated with Zn and conc. HCl to obtain the reduced bisbenzyl tertiary amines 23 and 22, respectively. When 23 and 22 were treated with trichloroisocyanuric acid (TCCA) in dichloromethane, oxidation at the benzyl position occurred, forming iminium ions. These intermediates were trapped by intramolecular reaction with the hydroxyls, and the resulting intermediates were then oxidized or shifted to afford 25 and 24, respectively. The entire one-pot process involves N-debenzylation, N-chlorination, and hemiacetal oxidation. The amine N-oxide-directed epoxidation complements Davies' ammonium-directed epoxidation. Thus, TCCA N-debenzylation is described for the first time and might be a useful N-debenzylation technique.

show abstract

Section: Resultsmentioning

confidence: 93%

Enantiospecific Total Synthesis of (+)-Tanikolide via a Key [2,3]-Meisenheimer Rearrangement with an Allylic Amine N-Oxide-Directed Epoxidation and a One-Pot Trichloroisocyanuric Acid N-Debenzylation and N-Chlorination

et al. 2013

View full text Add to dashboard Cite

show abstract

“…Trichloroisocyanuric acid (TCCA) is an inexpensive commercially available solid mainly reported to use for oxidation, chlorination, and dehydrogenation reactions. [11][12][13][14][15][16][17][18] To the best of our knowledge, there is no report on the synthesis of phosphoroamidates by the reaction of amines with dialkyl phosphates in the presence of TCCA in a one-pot manner. Therefore, we decided to study the feasibility of the TCCA as a safe reagent for the synthesis of phosphoroamidates under base-free conditions (Scheme 1).…”

Section: Paper Syn Thesismentioning

confidence: 99%

Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton–Todd Reaction under Base-Free Conditions

2017

View full text Add to dashboard Cite

A simple, efficient, and novel method is developed for the synthesis of phosphoroamidates via an Atherton–Todd coupling reaction of amines with dialkyl H-phosphite using trichloroisocyanuric acid as an efficient and safe reagent. Treatment of amines with dialkyl H-phosphite and trichloroisocyanuric acid under base-free conditions gives phosphoroamidates in moderate to good yields. The reaction proceeded effectively to afford the corresponding phosphoroamidates via a dehydrogenative coupling of H-phosphonates with amines. This method is easy, rapid, and good-yielding for the synthesis of phosphoroamidates.

show abstract

“…In the presence of anhydrous agents such as ferric chloride (88), hydrogen bromide, and acid chlorides, ethers react to form esters (see ETHERS). Esters can also be prepared from ethers by an oxidative process (89).…”

Section: Ch Chmentioning

confidence: 99%

Esterification

Aslam

Torrence

Zey

2000

Kirk-Othmer Encyclopedia of Chemical Technology

View full text Add to dashboard Cite

This discussion of esterification covers both the theoretical and practical implications of the technology. The kinetics and mechanism of esterification of carboxylic acids with alcohols are reviewed, along with factors affecting and methods for bringing about the completion of reaction. Several technical examples of esterification are given to demonstrate how the theory is applied. These examples include discussions of batch, continuous, and vapor‐phase processes. Methods for synthesizing esters from other compounds, such as acid anhydrides, acid chlorides, amides, nitriles, unsaturated hydrocarbons, ethers, aldehydes, and ketones are outlined. Numerous references and techniques are described. The process of esterification is also approached from the aspect of physical properties and characteristics. For example, a discussion on the synthesis of low, medium, and high boiling esters is given. Also, esterification techniques regarding difficulty esterifiable acids and ester interchange are described.

show abstract

Direct conversion of ethers to esters by trichloroisocyanuric acid

Cited by 26 publications

References 2 publications

Enantiospecific Total Synthesis of (+)-Tanikolide via a Key [2,3]-Meisenheimer Rearrangement with an Allylic Amine N-Oxide-Directed Epoxidation and a One-Pot Trichloroisocyanuric Acid N-Debenzylation and N-Chlorination

Enantiospecific Total Synthesis of (+)-Tanikolide via a Key [2,3]-Meisenheimer Rearrangement with an Allylic Amine N-Oxide-Directed Epoxidation and a One-Pot Trichloroisocyanuric Acid N-Debenzylation and N-Chlorination

Trichloroisocyanuric Acid as an Efficient Reagent for the Synthesis of Phosphoroamidates via Atherton–Todd Reaction under Base-Free Conditions

Esterification

Contact Info

Product

Resources

About