BT - Comprehensive Organic Synthesis

Although there have been a couple of interesting syntheses this week, I'm still very busy so I'm going to write about another Mulzer synthesis from my talk. See my for the background to this tribute.

1. To introduce basic concepts of organic synthesis:

3. To illustrate the importance of organic synthesis with real examples.

In fact one synthesis uses the following as carbon sources:

– a paper operation involving an imagined cleavage of a bond (yielding ‘synthons’) to suggest a method and possible SM’s for making the bond, ultimately leading to possible SM’s for the overall synthesis.

And illustrate their use in synthesis.

In planning a synthetic strategy, apart from devising a means of constructing the carbon skeleton with the required functionality as above, there are other subtle factors, which we must address.

Versatile reagents for the synthesis of conjugated polyenes, enones, and 1,3-oxathiole 1,1-dioxides

Thieme E-Journals - Synthesis / Abstract

It is not clear from this however, how the chemistry might be done! Therefore just being given the starting materials is not sufficient to help plan a synthesis.
Note the importance of CCBFR.

Wittig Synthesis of trans-9-(2-phenylethenyl) - Yumpu

We will illustrate this approach with examples, starting with synthesis of benzene derivatives. Starting point is usually fairly obvious – simple benzene derivatives or perhaps benzene itself.

[2,3]-Wittig Sigmatropic Rearrangements in Organic Synthesis

"The Wittig Reaction", Maercker, A. 1965, , 270. "Cycloalkenes by Intramolecular Wittig Reaction," Beeker, K. B. 1980,, 1717. "The Wittig Olefination Reaction of Carbonyl Compounds Other than Aldehydes and Ketones," Murphy, P. J. 1988, , 1. "The Wittig Olefination Reaction and Modifications Involving Phosphoryl-stabilized Carbanions. Stereochemistry, Mechanism, and Selected Synthetic Aspects," Maryanoff, B. E.; Reitz, A. B. 1989, , 863. "Synthesis of Heterocycles by the aza-Wittig Reaction," Gusar, N.I. 1991, , 146. "Stereochemistry and mechanism in the Wittig reaction," Vedejs, E.; Peterson, M. J. 1994, , 1. "Recent Synthetic Applications of the Non-Classical Wittig Reaction," Murphy, P. J.; Lee, S. E. 1999, 3049-66.

Guide to Tackling Multistep Synthesis Problems

The Wittig reagent [(diethoxyphosphinyl)methylidene]triphenylphosphorane (1b) has been successfully synthesized for the first time its phosphonium triflate salt (4a), by treating (diethoxyphosphinyl)methyl triflate with triphenylphosphine. The procedure has been applied to the synthesis of other phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various aldehydes and an activated ketone, affording the corresponding α,β-unsaturated phosphonates. Triphenylphosphorane 1b and triphenylphosphonium 4a led to both and isomers with the latter being predominant, while isomers were almost exclusively formed when tributyl reagents (1c and 4d) were used.

Thieme E-Books & E-Journals - Synthesis / Issue

We will discuss the results you obtained from the Wittig reaction you performed last week. You will also meet with your Synthesis Project Mentor sometime this week to go over your synthesis project.

The Wittig reaction-synthesis of trans-9-(2-phenylethenyl) ..

Georg Wittig (June 16, 1897 – August 26, 1987) was a German chemist who reported a method for synthesis of alkenes from aldehydes and ketones using compounds called phosphonium ylides in the Wittig reaction. He shared the Nobel Prize in Chemistry with Herbert C. Brown in 1979.