Reaction of a Highly Spiro-activated Electrophilic Cyclopropane with Pyridines; an Unusual Solvent Effect on Reaction Rate

DOI: 10.1039/P29860000043

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 43 - 48 (1986)

Update date:2022-08-05

Topics:

Authors:

Ohkata, Katsuo

Nagai, Takashi

Tamaru, Akira

Hanafusa, Terukiyo

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1039/P29860000043

The kinetics of the reaction of 3,3,10,10-tetramethyldispiro<5.0.5.1>tridecane-1,5,8,12-tetraone (1) with pyridine was studied in various pure solvents (protic and aprotic).Although this reaction afforded a polar zwitterion , the solvent effect on the reaction rate was not as remarkable as that in the Menschutkin reaction; it was related to Gutmann's DN parameters rather than to the Dimroth-Reichardt E_T values.The multiparameter analysis approach according to the Krygowski-Fawcett model in aprotic solvents and the Taft-Kamlet model in protic solvents was successful, giving log k₂ = -8.82 X E-3E_T - 17.4 X E-3DN - 3.36 (r = 0.927; n = 8) and log k₂ = -0.734α + 0.162β - 3.15 (r = 0.941; n = 6), respectively.Mechanisms are discussed.

Full text of DOI:10.1039/P29860000043

View Article Online / Journal Homepage / Table of Contents for this issue

View Article Online

Products guided by the article

Product name:C₂₃H₂₉NO₄

Cas No:83922-59-2

R&D Labs maybe for 83922-59-2

Onlychem (Jinan)Biotech Co.,Ltd

Contact:86-531-83175885

Address:No. 44, Honglou South Road, Jinan,China
Huayi Isotopes Co.

Contact:+ 86 512 52491118

Address:1 Fuyu Road, Haiyu TownChangshu, Jiangsu, China
Taizhou Shengxing Chempharm Co.,Ltd

Contact:+86-576-88516600

Address:Yantou Chemical Zone Jiaojiang Taizhou Zhejiang China
NINGBO YINLIANG FOREIGN TRADE CO., LTD.

Contact:+86-574-87834016 / 87898057

Address:23F NO.666JINYU ROAD,YINGZHOU DISTRICT,NINGBO.CHINA
X.T.Y Environ-Tech Co.,Ltd

Contact:+86-310-7092106

Address:Quzhou Modern & New Industrial Park, Handan, Hebei 057250, China

Relevant to this article

α,β,γ-trifluoroalkanes: A stereoselective synthesis placing three vicinal fluorines along a hydrocarbon chain

Doi:10.1021/ja045299q
(2005)
Studies toward the total synthesis of sorangicins: Asymmetric synthesis of the key fragments

Doi:10.1055/s-2004-835661
(2004)
REAKTIONEN VON CARBONYLCYCLOPENTADIENYLHYDRIDEN VON MOLYBDAEN UND WOLFRAM MIT α-AMINOACETYLENEN. II.

Doi:10.1016/S0022-328X(00)85852-0
(1982)
ACTIVATION OF CARBON DIOXIDE WITH ALUMINUM PORPHYRIN AND REACTION WITH EPOXIDE. STUDIES ON (TETRAPHENYLPORPHINATO)ALUMINUM ALKOXIDE HAVING A LONG OXYALKYLENE CHAIN AS THE ALKOXIDE GROUP.

Doi:10.1021/ja00343a038
(1983)
Synthesis of carumonam (AMA-1080) and a related compound starting from (2R,3R)-epoxysuccinic acid

Doi:10.1248/cpb.33.3798
(1985)
A mild and simple procedure for the reductive cleavage of acetals and ketals

Doi:10.1016/0040-4020(95)00055-D
(1995)

Article Doi