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trum (in KBr) indicated the presence of zwitterion formation. In accord with this structural assignment, refluxiiig I11 for 12 hours in 10% sodium carbonate solution gave rise to X-benzylpyrrole and I. This represents the first recorded Diels-Alder addition with a pyrrole acting as a diene. We hope
Organic Syntheses. Vol. 36. By hT. J . LEONARD, Editorin-Chief, John Wiley and Sons, Inc., 440 Fourth Avenue, hTew York 16, N. Y. 1956. vi 120 pp. 15.5 X 23.5 cm. Price, $3.75. “Tried and true” directions for preparing 35 organic m n p o u n d s are reported in I’oluine 36 of “Organic SJ-ritheses.” This volume rnaintaiiis tlie high standards of iLs predecessors in its editing, experimental directions :iiitl iiidexiiig. The compounds treated range from the very &nple, such as propiolaldehyde, t o t h e somewhat more complex, such as 3-hydroxycyclodecanone. T h e editor5 wisely refrain from including sl-ntheses of very complex compounds, which would have limited applicability and iiitercst . Probably one of tlie most useful pr one for diazomethane from fi-toly amide. T h e advantage of this method is t h a t t h e starting material is stable and soluble in organic solvents. This iiew volume will take its place as a worthy addition t~ tlic “Organic Syntheses” series, Tvliich has for many years lwcn one of tlie most valuable reference works for the organic clieinist.
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L)EPARTRIENT O F CHEMISTRY JOHN FISHER COLLEGE ) C H E S T E R , SE\V Y O R E ;
CARLJ. CIAUS
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The Chemistry of Petrochemicals. By MELVINJ. A s r L E , Professor of Chemistry, Case Institute of Technology, Cleveland, Ohio. Reinhold Publishing Corporation, 430 Park Avenue, S e w York 23, N. Y . 1956. v 267 pp. 16 X 23.5 cm. Price, $6.50. ’l‘liis voluine is a valua1)lc source of general iuformatioii : t i i t 1 literature references on organic chemical compounds IJroduced from petroleum. T h e 14 chapters contain 255 Imges of text, many equations and tables of d a t a , and 582 literature references. However, there is no author index a i i i l t h e bibliographies for each chapter are not alphabetic.illy arranged. The discussion i5 reniinisceiit of t h e books of Carleton Ellis. There is much useful information presented in .;iillicicnt detail t o introduce t h e reader t o -the subject. l:or example, alkylation is covered in 9 pages, 7 on alkylat i r i i i of paraffins and 2 on alkylation of aromatics. Two ; r i i t l otic-half pages are devotecl t o t h e theory of alkylation. l‘liis section is based almost entirely on t h e work of Schmerliiig. T h e bibliography oiriits sonic important papers in tliis field, particularly those of D r . P. D. Bartlett and ;i\zociates. T h e discussion of alkylation with hydrogen fluoride \t,irts off with the statement, “Hydrogen Fluoride is increasing in importance as an alkylation catalyst.” There is no mention of t h e fact t h a t HF alkylation was a n import a n t process for producing aviation alkylate during \X-orltl IVar 11, and t h a t nearly all of these HF alkylation plants I\ ere shut down, or converted t o other use, at the end of t h c witr. In rcg:irtl t o tlic Zieglcr priiccis (11. 103) fur pol>--
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Vol. 79
to report shortly on further rearrangements of the adduct and its hydrogenation products. LLOYA\IA?DLI I D~~~~~~~~~ OF cHEMIsTRk EMORY UNIVERSITY \VESL@,Y -4. B L A N C H A R U EMORY USIVERSITI’,GEORGIA RECEIVED MARCH28, 1937
olefins, it is iiow rnorc or less gciierallL- l;nov:ri that tiiisctl catalyses are better than aluminum alkyls alone. There are other spots in t h e text which itidicatc a lack of familiarity with Jvliat has actually been going on in iiidustfy. For example, on page 153, a process for concentrating henzene b y adsorption is described as though the plant 11x1 been built and operated. Actually this process for conccntrating benzene by adsorption never got beyond the draniiig h a r d stage. On t h e scientific side, there is a tendency toward ratlicr loose statements, such as t h e introductory sentence of chapter 2, which reads, “Inasmuch as petroleum is made L I P largely of paraffin hydrocarbons, these compounds must be considered t o be t h e ultimate starting materials for the ],reparation of petrochemicals.” Benzene and toluene occur in natural petroleum and have been separated conimcrcially as noted oii page 153. It is quite clear t l u t paraffins and c>-cloparafhs naturall~-occurring i i i petri)leurn are not the “ultiinate” starting materials for a i l petrochemicals. However, it is probably true t h a t o11 a tonnage basis, t h e clieinical. producctl from the para lliii atid cycloparaffin cr)nstituents of petroleum will probal,l!be more importcint tlian those produced from the tiaturLi11y occurring aromatics i l l pctroleuin. T h e title of this book illustrates t h c fact t h a t the uiird “petrochernical” is better adapted t o economic rather t l w i scientific discussion. 011 page 2 there is an estimatc that there will be 33 billion pounds of “ ~ ~ e t r o c l ~ e ~ ~ ~protliicetl icals” in 1936 of which 10.5 billion pounds n.ill be “inorgaiik. petrochemicals.” H i n r cvcr, t h e book omits eiitire1)- : ~ I I Y tliscussion of the clieniistr>. of t h e “inorg;t~iic~ i c t r o c l ~ v ~ ~ ~ i cals” such a s ammoiiia and sulfur. T h e n-ord “petroclii~tiiical,” a s ~ i ~ v it l l tlic pctrolcsiiiii iiidustry, brings together protliicti ~\-l~icli :LIT ccciiiornicail) related, b u t not clie~nicallyrel:itetl. I n spite of a certaiii degree of sulieriicialit!., \ \ l i i c ~ l i i-. perhaps unavoidable iii a hook covering so \vide 21 rtitigc t l f topics, this book should prove of real value t o tliow \ v l l i i need an introduction t o tlie field of tlic organic cliemistr!. ( I f hydrocarbons, and t h e more litnple orgwic cc>l~lpollli(lderivable from liydrocarlmis. S U N 011. C t J M P A Y Y
L ~ A R C I JHOOK, S PA. Polymer Iiic,,
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Solutions. Hy 1 1 . TOMPA..\c;iilciiiiL, I l l Fifth Aveiiue, S e w YorL i s , N. Y . : 2 5 pp. 10.0 X lfi.5 cm. Price YS.50.
1’1.~5,
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ziv 1liis is a coiiipreliensive review of currelit concept- ( i f ~ I I C holiition propertie3 of high polymeric suhstances. The author has wisely omitted a treatment of polyelectrolytes &ice this is more properly in the domain of electrolyte theory. Throughout, 111.. Toinpa compares theory with experimental results. ‘The book is practically self-contained. 1\11 t h e hasic formulas of the thermodynamics cif solutions and o f the statistics of coiled moleculcs are derived friim first principles. \Vhen t h e author disciiwes
