Revanna, Rajegowda H and Kumar, Raghavendra P and Hosamani, Amar and Siddagangaiah, Palakshamurthy B (2015) Efficient and practical synthesis of modular chiral beta-organochalcogeno amines, ArYCH2CH(R)NH2, and single crystal structures of (S) - MsOCH2CH(Bz)NH3+ center dot Cl- and (R)-MsOCH2CH(Ph)NH3+ center dot Cl-. In: JOURNAL OF ORGANOMETALLIC CHEMISTRY, 799-80 . pp. 61-69.
![]() |
PDF
Jou_Org_Che_799_61_2015.pdf - Published Version Restricted to Registered users only Download (1MB) | Request a copy |
Abstract
Modular chiral I3-organochalcogeno amines, ArYCH2CH(R)NH2 (4a-4g) where R = Me, Bz, Ph; and ArY = PhS, BzSe and 4-MeOC6H4Te respectively have been synthesized and characterized. Compounds 4a-4g were synthesized (Method II) from chiral aminoalkyl 13-methanesulfonate hydrochlorides, MsOCH2CH(R)NH3+ center dot Cl- (2a-2c) through nucleophilic displacement of MsO- with organochalcogenolate (ArY-). In another attempt (Method I) chiral beta-organotelluro amines (4a-4c) were prepared by deprotection of chiral N-boc I3-organotelluro amides, 4-MeOC6H4TeCH2CH(R)NH-Boc (3a-3c), which in turn, 13,-,1 were made from chiral N-boc 13-methanesulfonate amides (la-lc) and ArTeNa. 1H, and FTIR spectra of all the compounds (3a-3c and 4a-4g) were characteristic. The composition of 3a-3c was determined by elemental analysis. The a]TD values of 3b-3c and 4a-4g were determined. The single crystal structures of (S)-2b and (R)-2c were determined by X-Ray diffraction studies. Both (S)-2b and (R)2c were crystallized in orthorhombic system and the Flack parameter x was found 0.08(12) and 0.00(2) respectively. The crystal of (S)-2b contain two asymmetric units with gauche (A) and staggered (B) conformations. There are NH Cl-, NH-O and CH-O intra and intermolecular secondary interactions in (S)-2b and (R)-2c resulting in supramolecular structures. (C) 2015 Elsevier By. All rights reserved.
Item Type: | Journal Article |
---|---|
Publication: | JOURNAL OF ORGANOMETALLIC CHEMISTRY |
Publisher: | ELSEVIER SCIENCE SA |
Additional Information: | Copy right for this article belongs to the ELSEVIER SCIENCE SA, PO BOX 564, 1001 LAUSANNE, SWITZERLAND |
Keywords: | Chiral; beta-Chalcogen amine; Tellurium; Selenium |
Department/Centre: | Division of Chemical Sciences > Solid State & Structural Chemistry Unit |
Date Deposited: | 14 Jan 2016 05:19 |
Last Modified: | 14 Jan 2016 05:19 |
URI: | http://eprints.iisc.ac.in/id/eprint/53083 |
Actions (login required)
![]() |
View Item |