Chemical Name Reactions Guide
Chemists often refer to a particular type of reaction by name. Often, the reaction is given the names of the chemists who discovered, improved or promoted that particular reaction. Examples: Diels-Alder reaction, Claisen rearrangement, Sharpless epoxidation.
Contents:
What is the reaction?
I have the name of a reaction; how do I find out what the chemical reaction is?
Some good starting points:
- Merck Index (Science Library reference collection, RS 356 .M555, various editions). The Organic Name Reactions section provides an alphabetical listing with reaction diagrams (chemical structures), a brief text description, and citations to major papers or review articles on the reaction.
- Advanced organic chemistry: reactions, mechanisms, and structure, Jerry March. (Science Library reference collection or course reserves, QD 251.2 .M371 various editions). Look up the reaction name in the index to find a description & scheme, and citations to review article(s) on the reaction.
- Named Organic Reactions. Thomas Laue and Andreas Plagens (Science Library reference collection, QD 291 .L35 1998). Alphabetical arrangement with descriptions, schemes, examples, and citations to reviews and first articles on the reaction.
Find examples by keyword/topic.
I need to find a few specific examples (not all) of use of a named chemical reaction. What can I try? Also, I would like to find the examples in a specific journal. Example: find articles on the Mitsunobu reaction in Tetrahedron Letters.
Tip: a fulltext search often finds more examples than an abstract/title search, as it finds cases which are not the main point of the article.
Elsevier (ScienceDirect) ejournals
- Choose the Search tab on the top page navigation bar, then choose the Journals tab, and choose Chemistry from the pulldown Subject list.
- Enter the reaction name (e.g. Claisen rearrangement) within the Terms box; choose Full Text for Within, and then Search.
- If Full Text gives too many answers, try the Abstract, Title search within option instead.
American Chemical Society ejournals. To search a specific ejournal:
- Choose the Advanced Article Search tab.
- Under full-text search, select the particular journal to search (e.g. Journal of Organic Chemistry.) in the Specify Journal section.
- Key the reaction name (e.g. Sharpless epoxidation) into the Title or Abstract pulldown option in the Basic Search section and search.
- Tip - Try the Anywhere in Article option if the Title or Abstract search does not give enough examples.
- Tip - To find the name of the reaction in the article, choose the html format for the full article, then use the Find in Page menu option (in your web-browser) to locate the name of the reaction.
SciFinder Scholar (Chemical Abstracts).
- Use the Research Topic button and search by the reaction name.
- Note - this will often find very many (too many if you just need a few) possible answers.
- Choose Analyze or Refine, then Analyze by Journal Name. Also check the Sort Results Alphabetically box.
- Exit as soon as finished. This will free up a spot for someone else to use it. Scifinder only allows a few UMich users at a time.
General search tips: if a search on just the reaction name gives too many results, try:
- Limiting to selected publication year(s).
- Adding another search term using AND (or Refine search by Topic in SciFinder after completing the topic search), e.g. enantioselective AND diels alder reaction.
Find by chemical substructure/reaction search.
Beilstein. Note: Beilstein is the most comprehensive structure/ reaction searchable database - millions of reactions going back into the 1700's.
- Use the Structure editor to draw a general structure for the product and starting material(s).
- Tip: Beilstein assumes an exact structure unless told otherwise. You must specifically allow for substitution at the particular atoms where you want to have open substitution (substructure).
- Use the Editmode menu to switch to Reaction mode.
- Use the Select Tool (dashed box on left toolbar) to highlight a structure, then use the upper Product/Reactant buttons to specify whether it is a product or reactant..
- Use the crossed-arrows button to go to the main window, and select the Search button.
SciFinder Scholar. Note: a reaction search (specifying both reactant and starting material) in SciFinder will usually retrieve many fewer examples than using Beilstein. It searches a database (CASReacts) which includes fewer reactions which include: selected novel reactions (1987 - present), some classic older reactions, and reactions from a Russian database covering the 1970's and 1980's .
- Choose the Chemical Substance or Reaction button, then choose Chemical Structure button.
- Draw the reactant and product. Use the Add a Reaction Role tool (the AàB button) to specify reactant and product.
- Use the Get Reactions button to start the search.
- Tip: SciFinder Reaction Search assumes a general substructure search (unlimited substitution) to improve the likelihood of retrieving something. Because the database is selective (less complete), a particular specific reaction may not be indexed, so a substructure search improves the odds of finding a match. Even so, the search may sometimes be too general to complete. Beilstein, in contrast, almost always completes a search even if it takes a while.
- Tip: see the Chemical Abstracts Service guide to How to Explore by Reaction in SciFinder Scholar for additional help in getting started.
Review Articles
A scientific review article is an article summarizing/evaluating the research literature on a specific topic over a specific time period. They can often be an excellent starting point for exploring the literature.
Print sources
- Merck Index (Science Library reference collection, RS 356 .M555).
- March, Advanced Organic Chemistry (Science Library reference collection or course reserves, QD 251.2 .M371).
- Organic Reactions (Science Library reference collection, QD258 .O68). Each volume contains one or two long reviews with many examples of the name reaction.
Online sources:
SciFinder Scholar (Chemical Abstracts).
- Use the Research Topic search option. Search on a phrase with the reaction name (e.g. chiral catalysis of Diels Alder reactions).
- Once the initial search results are obtained, choose Analyze or Refine, then Refine.
- Choose Document Type.
- Check the box for Review.
Science Citation Index (aka WebofScience, ISI WebofKnowledge).
- Use the Full Search option and choose General Search.
- Type the reaction name (e.g. Diels Alder Reaction) into the Topic search box.
- Choose the "Restrict search by languages and document types . . ." option.
- Pick Review under the document type pull-down list.
- Exit the database when finished.
How do I get the articles?
See the Science Library's guide to How to find a Journal Article or use the MGet It Citation Finder. Note that the direct-link-to-article features are unavailable for the in-library (via UM Library Terminal Services) versions of SciFinder and Beilstein.
Need More Help?
For suggestions or additional chemistry literature research assistance contact David R. Peck (webpage).
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