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Chemistry

Science of Synthesis

What is Science of Synthesis?

science of synthesis logoScience of Synthesis is the 5th edition of the Houben-Weyl Methods in Organic Chemistry series, published by Thieme. It is a highly organized and authoritative collection of authored reviews on organic synthetic methods. Chapters contain experimental procedures, background information, and extensive yet selective bibliographies. Its purpose is to provide a direct path into the mass of primary literature on a wide range of organic reactions and products. The base set (48 volumes, 2000-2010) contains information on over 265,000 reactions and 29,000 experimental procedures. 

Organization

Each volume covers a specific class of compound, based on the target molecule to be synthesized. Volumes are organized into Categories, which are in turn broken down into narrower specialty volumes.

After 2010 SOS was continued by quarterly Knowledge Updates which contain updates of specific chapters from the original set. There are also occasional Reference Library topical monographs.  The Library has both series in print through 2015 and the Reference Library series as e-books through 2020.

SynOne is a free discovery tool that provides a way to search and browse the hierarchical chemical classification scheme and compound content of selected Thieme publications, including the entire Science of Synthesis series (and the journals Synlett and Synthesis from 2005 forward).  It is NOT a general/keyword search of these publications. 

Full Text

In 2021 UT Austin purchased e-book versions of the entire Science of Synthesis base set and the Reference Library through 2020.  However, the links in SynOne will not lead to the licensed and available e-book versions, even if you are in a proxied session.  (It links to the database version of SoS, which we do not subscribe to.)  See the next tab about SOS volumes for details on finding the e-book volumes.


Indexes

Each volume has keyword and author indexes, but there are no printed compound or formula indexes. Cumulative keyword and author index volumes were published for some Categories, but UT has only the index for Category 2 (vols. 9-17, Hetarenes). Since SOS is arranged hierarchically by product class, you can browse for compounds by class/volume, and use the hierarchical tables of contents to identify a volume of interest, then consult the keyword index of that volume.

SciFinder indexed most SOS chapters as general reviews, but not at the individual substance level. Knowledge Update chapters were only indexed in 2010-11.


Location

Science of Synthesis and Houben-Weyl 4th edition are currently located on the second level of the PMA Library, pending disposition of the Chemistry Collection. 

To find working book-level links to specific volumes, search a phrase, in quotation marks, from the volume title (see below) in the Library Catalog.  For example:

  • "boron compounds"
  • "six-membered hetarenes"

Or, the series title (in quotes) plus a volume number:

  • "science of synthesis" 26

Category 1. Organometallics.

  • v. 1. Compounds with transition metal-carbon [pi]-bonds and compounds of groups 10-8 (Ni, Pd, Pt, Co, Rh, Ir, Fe, Ru, Os) --
  • v. 2. Compounds of groups 7-3 (Mn..., Cr..., V..., Ti..., Sc..., La..., Ac...) --
  • v. 3. Compounds of groups 12 and 11 (Zn, Cd, Hg, Cu, Ag, Au) --
  • v. 4. Compounds of group 15 (As, Sb, Bi) and silicon compounds --
  • v. 5. Compounds of group 14 (Ge, Sn, Pb) --
  • v. 6. Boron compounds --
  • v. 7. Compounds of groups 13 and 2 (Al, Ga, In, Tl, Be ... Ba) --
  • v. 8a-8b. Compounds of group 1 (Li ... Cs)

Category 2. Hetarenes and related ring systems.

  • v. 9. Fully unsaturated small-ring heterocycles and monocyclic five-membered hetarenes with one heteroatom --
  • v. 10. Fused five-membered hetarenes with one heteroatom --
  • v. 11. Five-membered hetarenes with one chalcogen and one additional heteroatom --
  • v. 12. Five-membered hetarenes with two nitrogen or phosphorus atoms --
  • v. 13. Five-membered hetarenes with three or more heteroatoms --
  • v. 14. Six-membered hetarenes with one chalcogen --
  • v. 15. Six-membered hetarenes with one nitrogen or phosphorus atom --
  • v. 16. Six-membered hetarenes with two identical heteroatoms --
  • v. 17. Six-membered hetarenes with two unlike or more than two heteroatoms and fully unsaturated larger-ring heterocycles -

 

Category 3. Compounds with four and three carbon-heteroatom bonds.

  • v. 18. Four carbon-heteroatom bonds: X-C---X, X--C--X, X₂C--X, CX₄ --
  • v. 19. Three carbon-heteroatom bonds: nitriles, isocyanides, and derivatives --
  • v. 20a. Three carbon-heteroatom bonds: acid halides; carboxylic acids and acid salts --
  • v. 20b. Three carbon-heteroatom bonds: esters and lactones; peroxy acids and R(CO)OX compounds; R(CO)X, X=S, Se, Te --
  • v. 21. Three carbon-heteroatom bonds: amides and derivatives; peptides; lactams --
  • v. 22. Three carbon-heteroatom bonds: thio-, seleno-, and tellurocarboxylic acid and derivatives; imidic acids and derivatives; ortho acid derivatives --
  • v. 23. Three carbon-heteroatom bonds: ketenes and derivatives --
  • v. 24. Three carbon-heteroatom bonds: ketene acetals and Yne-X compounds

 

Category 4. Compounds with two carbon-heteroatom bonds.

  • v. 25. Aldehydes --
  • v. 26. Ketones --
  • v. 27. Heteroatom analogues of aldehydes and ketones --
  • v. 28. Quinones and heteroatom analogues --
  • v. 29. Acetals: Hal/X and O/O,S,Se,Te --
  • v. 30. Acetals: O/N, S/S, S/N, and N/N and higher heteroatom analogues --
  • v. 31a. Arene-X (X=Hal,O,S,Se,Te) -- v. 31b. Arene-X (X=N,P) --
  • v. 32. X-Ene-X (X=F, Cl, Br, I, O, S, Se, Te, N, P), Ene-Hal, and Ene-O compounds --
  • v. 33. Ene-X compounds (X=S, Se, Te, N, P)

 

Category 5. Compounds with one saturated carbon-heteroatom bond.

  • v. 34. Fluorine --
  • v. 35. Chlorine, bromine, and iodine --
  • v. 36. Alcohols --
  • v. 37. Ethers --
  • v. 38. Peroxides --
  • v. 39. Sulfur, selenium and tellurium --
  • v. 40a. Amines and ammonium salts --
  • v. 40b. Amine N-Oxides, haloamines, hydroxylamines and sulfur analogues, and hydrazines --
  • v. 41. Nitro, nitroso, azo, azoxy, and diazonium compounds, azides, triazenes, and tetrazenes --
  • v. 42. Organophosphorus compounds (incl. RO-P and RN-P)

 

Category 6. Compounds with all-carbon functions.

  • v. 43. Polyynes, arynes, enynes, and alkynes --
  • v. 44. Cumulenes and allenes --
  • v. 45a. Monocyclic arenes, quasiarenes, and annulenes --
  • v. 45b. Aromatic ring assemblies, polycyclic aromatic hydrocarbons, and conjugated polyenes --
  • v. 46. 1, 3-Dienes --
  • v. 47. Alkenes --
  • v. 48. Alkanes

 

The 4th Edition was titled Methoden der organischen Chemie and was published from 1952 to 2003.  Volumes were in German until 1990. The base set was supplemented by an extensive "E-series" that began in 1982. With 160 volumes and over 160,000 pages, the 4th edition was much larger than its successor and can still be consulted for information that was not updated in SOS. A brief printed User's Guide offers a handy list of volumes with the compound types covered in each. Volumes E23, parts O-P, are a synopsis of the HW structure and detailed tables of contents in English for all volumes.

Indexes

Vol. 16 of the 4th edition base set comprises indexes by experimental procedure and substance class for the 4th edition and selected supplementary volumes (E1-E5 and E11, i.e. through about 1986). Volume E23 is a multi-part structural formula index of reaction products by compound class, but its arcane arrangement makes it essentially impossible to use. As with SOS, the best approach is to use its hierarchical organization to identify a volume and then look in that volume directly.

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