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Synthesis and Structure of Tetrahydro‐4,7‐ethanoisobenzofuran‐1,3‐dione Derivative
Author(s) -
Fang Mingfeng,
Pan Chunmeng,
Lu Song,
Lin Zhongxiang,
Lu GuoYuan
Publication year - 2015
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201500161
Subject(s) - chemistry , adduct , isomerization , crystal structure , two dimensional nuclear magnetic resonance spectroscopy , dept , derivative (finance) , heteronuclear single quantum coherence spectroscopy , maleic anhydride , cycloaddition , stereochemistry , nmr spectra database , crystallography , catalysis , organic chemistry , spectral line , polymer , physics , copolymer , astronomy , financial economics , economics
(1 R ,2 R ,3 S ,4 R ,7 R )‐7‐Isopropyl‐6‐methylbicyclo[2.2.2]oct‐5‐ene‐2,3‐dicarboxylic acid anhydride (tetrahydro‐4,7‐ethanoisobenzofuran‐1,3‐dione derivative) adduct 2 was prepared via the isomerization of α ‐pinene and β ‐pinene in turpentine followed by the Diels‐Alder cycloaddition with maleic anhydride in the presence of phosphoric acid/iodine catalysis. The molecular structure of adduct 2 was characterized by IR, 1 H NMR, 13 C NMR, 1 H‐ 1 H COSY, DEPT, HSQC, HMBC, 2D NOESY and MS spectra. The single crystal X‐ray crystallographic analysis of adduct 2 was performed, and the X‐ray powder diffractive spectrum of the sample adduct 2 is consistent with the diffractive spectrum calculated from the single crystal data. Therefore the structure and stereochemistry of adduct 2 was established based on extensive spectral data and single crystal X‐ray analysis.