How to Use Beilstein, SciFinder, and the Rest of the Literature Properly

1. Don't use the literature or the lecture notes to the exclusion of the other. All of the assigned problems can be solved using one of the reactions we have discussed in class. Look for retrons in the products that signal transformations we have discussed, and use these retrons to guide your thinking about possible disconnections.

2. Use substructure searching (free sites, single/double bonds) in Beilstein and SciFinder to search for substrates similar to yours that undergo a particular reaction. Use the reaction mode to find out how a particular product has been made.

3. When you find a reaction in the literature that is similar to the one you want to carry out, be sure that the cited substrate for the reaction is similar to the substrate on which you want to carry out the same reaction. Changes in steric crowding around the reaction center, the presence of other functional groups, and even changes in volatility can alter the reaction course. (A 400 °C gas-phase reaction that works well on ethane may not work so well on 4-phenyl-2-methylheptane.) Be mindful of the potential side reactions that your particular substrate can undergo.

4. Do not cite reactions for which you cannot draw mechanisms. Nine times out of ten, if you do not understand how a reaction works, then you will misapply it in your particular synthetic problem. This is especially true of reactions from the patent literature and reactions that are shown to work only on very simple substrates such as ethane and propene.

5. Never cite an article without looking it up. To ensure that you have looked up the article, all references cited in your homework must be accompanied by a photocopy or printout of the first page of the article and the page of the article on which the cited reaction appears, and the cited reaction and conditions must be circled in red or highlighted. A Beilstein or SciFinder Scholar citation is not an original literature reference and will be disregarded.

   I've created a Web page that has links to the common organic chemistry journals. Most, but not all, of the articles you will need are available online. Notable exceptions include Elsevier journals (the Tetrahedron family) from before 1995. If an article is not available online, hie thy butt down to the library and look it up manually!

6. Never cite an article without reading it. Sometimes the text tells you the limitations of the reaction you are citing. You cannot glean such information only by looking at pictures.

   If the article is in a language you don't know, find someone who can read it for you. I can read French, and I can fight my way through German. Our library carries translations of Zh. Obshch. Khim. (formerly J. Gen. Chem. USSR, now Russ. J. Gen. Chem.) and Zh. Org. Khim. (formely J. Org. Chem. USSR, now Russ. J. Org. Chem.). There has been an English version of Angew. Chem. (Angew. Chem. Intl. Ed.) since about 1964. Most of the European journals (Liebigs Ann., Helv. Chim. Acta, Coll. Czech Chem. Commun.) have carried many of their articles in English since the 1970s. The Beilstein or SciFinder citation tells you in what language an article is written and whether there is an English translation ("Engl. Ausg."). The page numbers usually differ between the original language and the translation. (The German for page is Seite, abbreviated S.)

7. Cite articles using American Chemical Society conventions:

   typed: I. M. Author, C. M. Work. Journal Name Year, Volume, first page.
   handwritten: I. M. Author, C. M. Work. Journal Name Year, Volume, first page.

   Notes:
   • Some journals (e.g., all British journals) don't have volume numbers.
   • Don't confuse volume numbers with issue numbers. Do not include the issue number in your citation.
   • Do not include Beilstein's six-letter journal code.
   • Beilstein sometimes cites the page on which an article begins, sometimes the page on which a reaction appears, and sometimes both. Cite only the page on which the article begins. Make sure you look up the article to check that you are citing the right page (see above).

8. One of the problems with the online databases is that the forest can't be seen for the trees. The literature is full of bad reactions, and Beilstein and SciFinder do not allow you to judge whether a particular transformation has been widely accepted or even repeated by another group.

   Places to look for discussions of reactions' scope, limitations, and mechanisms:

   • Organic Reactions -- organized by reaction -- articles there include long tables citing every example of the reaction under review that appeared until the time the article was written
   • Houben-Weyl's Methoden -- organized by functional group
   • Comprehensive Organic Transformations -- organized by transformation
   • Review articles -- A list of almost all English-language organic chemistry review articles ever written can be obtained.

9. If you find a nice paper or review article describing a particular chemistry and you want to know who has recently cited that paper, you can use Web of Science to obtain this information.

Back to CHE 535 home page.