NMR analysis of (1S, 1aR, 6aR)-2’, 3’, 6, 6a-tetrahydrospiro cycloprop a indene-1(1aH), 1’- 1H indene

Abstract

The aldol condensation product of 1H-indan-1-one, (2E)-2-(2,3-dihydro-1H-in den-1-ylidene)-2,3-dihydro-1H-inden-1-one, subjected to Huang–Minlon reduction conditions was shown, via 1D and 2D NMR analysis, to be a mixture of (1S,1aR,6aR)-2’,3’,6,6a-tetrahydro-spiro cycloprop a indene-1(1aH),1’ 1H indene and its 1R,1aS,6aS enantiomer and not 2,3,1’,3’-tetrahydro- 1,2’ -biindenylidene as originally expected. The full NMR assignment, the coupling constants in the proton NMR, and the couplings in the HMBC and NOESY of the title compound are summarized in the Table.

Pokazano je pomoću 1D i 2D NMR analize da (2E)-2-(2,3-dihidro-1H-inden-1-iliden)-2, 3-dihidro-1H-inden-1-on, dobiven aldolnom kondenzacijom 1H-indan-1-ona, podvrgnut Huang–Minlonovoj redukciji daje smešu (1S,1aR,6aR)-2’,3’,6 6a-tetrahidro-spiro[cikloprop[a]inden-1(1aH),1’-[1H]indena] i njegovog 1R,1aS,6aS enantiomera, a ne 2,3,1’,3’-tetrahidro-[1,2’]-biindeniliden kako se prvobitno očekivalo. Potpuni NMR raspored, konstante kuplovanja protona i HMBC i NOESY kuplovanje jedinjenja u naslovu dati su zbirno u tabeli.