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While the pyrroles produced by the Piloty-Robinson
Synthesis are often very useful, the reaction itself is not always favorable because it requires high temperatures and long reaction times in addition to the problems mentioned above, the yield is often low or moderate. Modern methods have alleviated
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held a
Sectional Dinner to which, according to tradition, only men were invited. Gertrude Robinson hosted “a dinner party at the same time as the Sectional Dinner, in the same hotel and with the same menu, to which she invited other women chemists as well as wives of the sectional officers and of
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The
Robinsons investigated the structure of leucoanthocyanins, colorless molecules that generate anthocyanidins and are present in most plants. Rosenheim simultaneously discovered leucoanthocyanins and he coined the term. Leucoanthocyanins occur in more locations (wood, bark, nutshells, flowers,
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Besides her work as a chemist, Gertrude
Robinson had two children, Marion in 1921 and Michael in 1926. She was an avid mountain climber, a prolific traveler, and a frequent hostess. Perhaps inspiring her work on plant pigments, she and her husband also kept a garden for many years.
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514:, which was removed during a step in the hydrolysis. While she did not solve this problem, she did improve the yield and decrease the dialdehyde recovered by “the acylation of a substituted ethyl acetoacetate by the group related to the weakest possible acid”.
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This reaction, originally named after Piloty, had the
Robinson name added to it due to their work on the mechanism. While it is unclear which Robinson the synthesis is technically named after, the paper on the topic was authored by both Gertrude and Robert.
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One of the drawbacks of the
Robinsons’ methods for the synthesis of fatty acids are the low yields due to the recoveries of a significant portion of the dialdehyde. The justification by Gertrude Robinson for this low yield was that the
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azine derived from a ketone. Also, under high temperatures and highly acidic solutions, azines derived from aldehydes are not stable. This prevents the formation of 2,5-disubstituted pyrroles (where R=H) using this method.
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One example of this is the synthesis of 10-ketotridecoic acid via 13-diketopalmitic acid, which is an important acid because, with reduction and dehydration, it becomes the molecule that is an active ovarian hormone.
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Move in-body footnote text to either proper "notes" end section or else include content in article proper. Capitalization MOS in headings and captions; would also be useful to add DOI to refs.
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and lactarinic acid. Her methods led to her synthesis of fatty acids with the greatest molecular weights of the time (specifically, tricontanoic and 13-oxodotetracontanoic acids).
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The
Robinsons disproved many of the prevailing theories about the Fischer Indole Mechanism by showing that the reaction went unperturbed in the presence of other
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The
Robinsons, who lacked a machine with which to extract pigments, instead would cover the relevant plants with boards and then drive back and forth over them.
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of lactarinic acid. They then synthesized 6-ketostearic acid via a reaction of ethyl sodio-2-acetyl-n-tridecoate and 5-carbethoxyvaleryl chloride and then
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210:, she was granted her B. Sc. in 1907 and M. Sc. in 1908 from Owens College. She then researched at the University of Manchester under
271:, the couple provided a method for synthesizing tetraphenylpyrrole . The Piloty-Robinson Pyrrole Synthesis is named in their honor.
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Robinson was born on 6 February 1886 in
Winsford, Cheshire and died of a heart attack on 1 March 1954. After attending
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There are, however, a few problems with some syntheses. The Piloty-Robinson reaction competes with the formation of
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other prominent members.” Following this event, all dinners of the
British Association have been open to women.
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in London. She worked on the syntheses of saturated and unsaturated fatty acids and was the first to synthesize
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decreases the time necessary for the reaction from around 3 days to 30-60 min. It can also affect the yield.
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with her husband. She was the first to observe that the color of a plant’s pigment was not related to the
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and with whom she coauthored many papers, and moved to the position of an unpaid demonstrator at the
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The conversion of azines to 3,4-disubstituted pyrroles using the Piloty-Robinson Pyrrole Synthesis.
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The mechanism for the Piloty-Robinson Pyrrole Synthesis suggested by Gertrude and Robert Robinson.
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Gertrude Robinson, using her methods for the synthesis of higher fatty acids, synthesized
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Organic Preparations and Procedures International: The New Journal for Organic Synthesis
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Medawar, P.B.; Robinson, G.M.; Robinson, R. A Synthetic Differential Growth Inhibitor.
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The Robinsons identified the location of the double bond in, and also synthesized,
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Milgram, B.C.; Eskildsen, K.; Richter, S.M.; Scheidt, W.R.; Scheidt, K. A.
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Example of a Piloty-Robinson Pyrrole Synthesis via Microwave Irradiation
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Chemistry Was Their Life: Pioneering British Women Chemists, 1880-1949
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The precursor to cyanidin chloride (an anthocyanidin) and its tautomer
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She also independently suggested the asymmetric structure of aromatic
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Flowers, fruits, and leaves get their pigments from anthocyanins and
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267:. Based on this mechanism and working off the pyrrole syntheses of
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Dunstan, A.E.; Woodhead, D.W.; Simonsen, J.L. Obituary notices.
535:, also known as Melissic acid, and 13-oxodotetracontanoic acid.
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most famous for her work on plant pigments; the Piloty-Robinson
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Lawrence, W. J. C.; Price, J.R.; Robinson, G.M.; Robinson, R.
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The Fischer Indole Mechanism as interpreted by the Robinsons.
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properties. In 1953, the University of Oxford granted her an
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offer an easier and more efficient workup and purification.
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Example of the Robinsons' synthesis of tetraphenylpyrrole
491:
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Gertrude Robinson's synthesis of n-triacontanoic acid.
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Example of a solid-supported Piloty-Robinson Synthesis
263:
and, with her husband, postulated a mechanism for the
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Synthesis, which is named for her; her syntheses of
613:British Association for the Advancement of Science
918:Comprehensive Organic Name Reactions and Reagents
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931:Name Reactions and Reagents in Organic Synthesis
719:, Imperial College Press: London, 2008. 435-438.
1129:Alumni of the Victoria University of Manchester
760:The Biographical Dictionary of Women in Science
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397:The mechanism as suggested by the Robinsons.
576:Lactarinic Acid, isolated from fungi of the
595:to prove the structure of lactarinic acid.
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929:Mundy, B.P.; Ellerd, M.G.; Favaloro, F.G.
521:Robinsons synthesis of higher fatty acids.
497:Methods of Synthesis of Higher Fatty Acids
966:Tanaka, H..; Moriwaki, M.; Takahashi, T.
933:, 2nd ed.; Wiley: Hoboken, 2005, 510-511.
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373:to 3,4-disubstituted pyrroles.
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236:before briefly going to the
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311:Anthocyanins and Copigments
52:. The specific problem is:
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468:Fischer Indole Mechanism
426:some of these concerns.
412:when the reactant is an
265:Fischer Indole Synthesis
19:Not to be confused with
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585:Beckmann Transformation
208:Verdin Secondary School
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533:n-triacontanoic acid
296:honorary M.A. degree
276:University of Oxford
274:After moving to the
234:University of Sydney
224:In 1912 she married
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48:to meet Knowledge's
506:intermediate was a
435:Microwave radiation
119:, Cheshire, England
103:Gertrude Maud Walsh
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242:University College
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1077:KNAW, Proceedings
339:Leucoanthocyanins
288:leucoanthocyanins
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168:Organic chemistry
158:Scientific career
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41:This article may
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333:ferric chloride
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184:organic chemist
151:Robert Robinson
137:Alma mater
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113:6 February 1886
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130:(1954-03-01)
128:1 March 1954
73:
67:October 2019
64:
57:Please help
53:
42:
25:
1109:1954 deaths
1104:1886 births
753:Ogilvie, M.
512:acetic acid
508:weaker acid
421:Modern Uses
238:St. Andrews
230:Nobel Prize
192:fatty acids
61:if you can.
1098:Categories
1087:, 773-778.
1046:, 175-180.
1000:, 745-751.
968:Org. Lett.
904:, 171-210.
880:, 639-645.
837:, 206-212.
757:Harvey, J.
633:References
593:hydrolysis
555:oleic acid
549:Oleic Acid
476:such as p-
410:pyrazoline
325:immiscible
317:copigments
292:antibiotic
246:oleic acid
196:penicillin
109:1886-02-06
916:Wang, Z.
578:Lactarius
478:toluidine
414:aliphatic
321:flavonols
202:Biography
848:Biochem.
831:Biochem.
811:Biochem.
794:Biochem.
504:aldehyde
117:Winsford
43:require
657:, 195.
587:on the
329:alkalis
188:Pyrrole
45:cleanup
1066:, 442.
1056:Nature
647:Nature
371:azines
269:Piloty
164:Fields
147:Spouse
599:Notes
589:oxime
581:genus
510:than
1081:1904
1060:1911
1040:1925
1018:1934
998:1930
972:2003
951:2007
902:45:3
898:2013
874:1918
852:1938
835:1932
815:1931
798:1934
777:1939
734:2011
692:1954
651:1943
611:The
125:Died
99:Born
1044:127
953:,
878:113
696:doi
659:doi
655:151
331:or
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284:pH
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698::
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107:(
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