Synthesis of 4-Substituted Thianaphthene Derivatives

Kloetzel, Milton C.; Little, Jess E.; Frisch, David M.

doi:10.1021/jo50017a009

Cited by 19 publications

(10 citation statements)

References 5 publications

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“…of auxin action. However, by analogy with the naphthalene acetic acids, one would expect the 3-, 4-, and 7-TAA to have growth-regulating activity and evidence for this has been produced for the 3-and 7 -acids, and the 4-acid had previously been shown to be an auxin (Kloetzel, Little, and Frisch 1953).…”

Section: Biological Testingmentioning

confidence: 99%

“…Since thionaphthen-3-acetic acid (3-TAA) (I) was found to be an auxin (Crook, Davies, and Smith 1937) attempts have been made to prepare and test biologically :t----;;,""-' -CH2 -C02H (I) all the isomeric thionaphthenacetic acids. This has been done with the exception of thionaphthen-4-acetic acid (4-TAA), which was synthesized and shown to be an auxin by Kloetzel, Little, and Frisch (1953).…”

Section: Introductionmentioning

confidence: 99%

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Sulphur Analogues of Indoleacetic Acid: Synthesis and Biological Activity of some Thionaphthenacetic Acids

Kefford¹,

Kelso²

1957

Aust. Jnl. Of Bio. Sci.

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The thionaphthen�2�, �3-, -5-, -6�, and -7-acetic acids have been synthesized from the chlorides of the corresponding carboxylic acids by the Arndt-Eistert reaction and their plant growth-regulating activities, as indicated by their effects upon protoplasmic streaming, have been compared with those of indole-3-acetic acid (IAA) and 2,4-dichlorophenoxyacetic acid (2,4�D). The thionaphthen-3- and -7- acetic acids and IAA have similar effects upon protoplasmic streaming, while the effects of the thionaphthen-2-, -5-, and �6-acetic acids differ from those of IAA and resemble in part those of 2, 4-D.

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Section: Biological Testingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Sulphur Analogues of Indoleacetic Acid: Synthesis and Biological Activity of some Thionaphthenacetic Acids

Kefford¹,

Kelso²

1957

Aust. Jnl. Of Bio. Sci.

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“…Irradiation of 1 x M solutions of 1-phenyl-4-(2'-thieny1)-l,3-butadiene (1) in dry benzene containing 2 x M iodine gave, after 3 days, 4-phenylbenzo[b]thiophene (2), in 15% yield, identical to the known compound (10). As shown in Scheme 1, photocyclization of 1 can occur to the thiophene ring t o give 2, as observed, or photocyclization can occur to the phenyl group to give the known 1-(2'-thieny1)naphthalene (3) (1 1 For personal use only.…”

mentioning

confidence: 99%

Photocyclization Reactions of Aryl Polyenes. VII. The Photocyclization of 1-Phenyl-4-thienyl- and 1,4-Dithienyl-1,3-butadienes

Leznoff¹,

Lilie²,

Manning³

1974

Can. J. Chem.

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The photocyclization–oxidation reaction of 1-phenyl-4-(2′-thienyl)-1,3-butadiene gave 4-phenyl-benzo[b]thiophene. Similarly, irradiation of 1-phenyl-4-(3′-thienyl)-l,3-butadiene gave 7-phenylbenzo-[b]thiophene. Thus, photocyclization occurs exclusively to the thiophene ring. Irradiation of 1,4-di(2′-thienyl)-1,3-butadiene and 1,4-di(3′-thienyl)-1,3-butadiene yielded 4-(2′-thienyl)benzo[b]thiophene and 7-(3′-thienyl)benzo[b]thiophene, respectively. Photocyclization of 1-(2′-thienyl)-4-(3″-thienyl)-1,3-butadiene gave an inseparable mixture of 4-(3′-thienyl)benzo[b]thiophene and 7-(2′-thienyl)benzo[b]thiophene.

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“…While preparing a number of conformationally biased compounds, 3-(hydroxymethyl)-4,4-dimethylpentanoic acid -lactone (7) was required as part of a synthetic scheme. It has been shown on several occa-sions28-0 that the material obtained from the dehydration of ethyl 3-hydroxy-3,4,4-trimethylpentanoate (lc) gives 4-hydroxy-3,3,4-trimethylpentanoic acid -lactone (2) rather than 7 as originally thought.2d We have synthesized 7 in 62% yield from lc and now summarize our work.…”

mentioning

confidence: 99%

“…The lactone 7 was prepared by the route shown in Scheme I. Using the procedure of Newman2 and Heilman,3 the hydroxy ester lc was dehydrated in good yield to give the two unsaturated esters 3 and 4 in equal amounts.…”

mentioning

confidence: 99%

Preparation of 3-(hydroxymethyl)-4,4-dimethylpentanoic acid .gamma.-lactone

DeBoer¹,

Hunter²

1973

J. Org. Chem.

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DeBoer and Hxjnter tance reading recorded. By noting the direction of any drift and its magnitude, and assuming the drift to be constant throughout the run, the corrected infinity point was calculated. Rate constants were then calculated using the hatsol2 computer program (see above). In several runs, we have plotted the concentrations of substrate from the computer output and found excellent first-order behavior over the 2 half-fifes examined.Using the above procedure with the M-D Mini-Cell,15 30 ml of 10_s M substrate solution is adequate to produce duplicate rate constants at two temperature and potentiometrically determined infinity titer checks at both temperatures.

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Synthesis of 4-Substituted Thianaphthene Derivatives

Cited by 19 publications

References 5 publications

Sulphur Analogues of Indoleacetic Acid: Synthesis and Biological Activity of some Thionaphthenacetic Acids

Sulphur Analogues of Indoleacetic Acid: Synthesis and Biological Activity of some Thionaphthenacetic Acids

Photocyclization Reactions of Aryl Polyenes. VII. The Photocyclization of 1-Phenyl-4-thienyl- and 1,4-Dithienyl-1,3-butadienes

Preparation of 3-(hydroxymethyl)-4,4-dimethylpentanoic acid .gamma.-lactone

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