DOI: 10.1002/recl.19590780509. Orthothioesters and 1,1‐bis‐(ethylthio)‐1‐alkenes (thioacetals of ketenes)

Orthothioesters and 1,1‐bis‐(ethylthio)‐1‐alkenes (thioacetals of ketenes)

10.1002/recl.19590780509

Crossref journal-article

Wiley

Recueil des Travaux Chimiques des Pays-Bas (311)

Abstract

AbstractA number of ethyl orthothioesters has been prepared by refluxing acid chlorides with ethanethiol and zinc chloride. The substances very easily lose one mole of ethanethiol by distillation in the presence of traces of acids, affording the thioacetals of substituted ketenes VII. The structure of the latter compounds follows from the hydrolysis of their sulphones VIII into the next lower aldehydes IX and bis (ethanesulphonyl) methane X.It is pointed out, that interesting reactions can be carried out by making use of various methods for the introduction and elimination of thioether groups (see reaction schemes on pages 5 and 6).

Bibliography

Rinzema, L. C., Stoffelsma, J., & Arens, J. F. (1959). Orthothioesters and 1,1âbisâ(ethylthio)â1âalkenes (thioacetals of ketenes). Recueil Des Travaux Chimiques Des Pays-Bas, 78(5), 354â363. Portico.

Authors 3

L. C. Rinzema (first)
J. Stoffelsma (additional)
J. F. Arens (additional)

References 25 Referenced 36

10.1002/recl.19570761102
J. D.Kendall(Ilford Ltd.) Brit. Pat. 556 815
Chem. Abstr.1945 18802;
U.S. Pat. 2 389 153
Chem. Abstr.1946 15403).
10.1021/ja01103a044
CompareH. W.Post “The Chemistry of Aliphatic Ortho Esters” New York1943 p.20and27.
{'key': 'e_1_2_1_5_2', 'first-page': '193', 'volume': '15', 'author': 'Claesson P.', 'year': '1877', 'journal-title': 'J. prakt. Chem. [2]'} / J. prakt. Chem. [2] by Claesson P. (1877)
10.1002/recl.19330520514
10.1002/recl.19460650108
We are very much indebted to Professor E. D. Hughes of University College London who suggested this explanation during a discussion with one of us (A).
10.1002/recl.19590780405
10.1002/recl.19580771210
10.1021/ja01128a071
10.1002/cber.19550880419
{'key': 'e_1_2_1_10_2', 'first-page': '43', 'volume': '60', 'author': 'Volger H. C.', 'year': '1957', 'journal-title': 'Proc. Koninkl. Nederland. Akad. Wetenschap.'} / Proc. Koninkl. Nederland. Akad. Wetenschap. by Volger H. C. (1957)
E.Rothstein J. Chem. Soc.1940 1553. (10.1039/JR9400001553)
Observed constants of the thioesters: R = CH3: b.p. 115–117° nD28 1.4503; R = C2H5: b.p. 134–137° nD20 1.4595; R = n‐C7H15; b.p. 97–98° (3 mm) nD20 1.4632.
Literature values: b.p. 188.5–188.9° nD20 1.4551 (E. C. E.HunterandJ. R.Partington J. Chem. Soc.1932 2819.
{'key': 'e_1_2_1_13_2', 'first-page': '1753', 'volume': '60', 'author': 'Bell F. K.', 'year': '1927', 'journal-title': 'Ber.'} / Ber. by Bell F. K. (1927)
Organic Syntheses Coll. Vol. III 382.
Prepared according to the instructions inA.Vogel “Practical Organic Chemistry” 1st. Ed. London1948 p.768 working at −25° instead of at −10°. Yield 65–75% of the theoretical.
{'key': 'e_1_2_1_16_2', 'first-page': '620', 'volume': '33', 'author': 'v. Pechmann H.', 'year': '1900', 'journal-title': 'Ber.'} / Ber. by v. Pechmann H. (1900)
A larger batch required a longer reaction time.
10.1002/cber.19570900709

Dates

Type	When
Created	14 years, 11 months ago (Sept. 14, 2010, 1:16 a.m.)
Deposited	1 year, 9 months ago (Nov. 13, 2023, 3:06 p.m.)
Indexed	1 year, 7 months ago (Jan. 18, 2024, 3:32 a.m.)
Issued	66 years, 8 months ago (Jan. 1, 1959)
Published	66 years, 8 months ago (Jan. 1, 1959)
Published Online	15 years ago (Sept. 2, 2010)
Published Print	66 years, 8 months ago (Jan. 1, 1959)

Funders 0

None

BibTeX

@article{Rinzema_1959, title={Orthothioesters and 1,1‐bis‐(ethylthio)‐1‐alkenes (thioacetals of ketenes)}, volume={78}, ISSN={0165-0513}, url={http://dx.doi.org/10.1002/recl.19590780509}, DOI={10.1002/recl.19590780509}, number={5}, journal={Recueil des Travaux Chimiques des Pays-Bas}, publisher={Wiley}, author={Rinzema, L. C. and Stoffelsma, J. and Arens, J. F.}, year={1959}, month=jan, pages={354–363} }

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