Lewis acid mediated rearrangements of spiro[2.n]alkane-1,1-dicarboxylates (n = 2–5): an experimental evidence of stepwise 1,2-zwitter-ion formation

Lewis acid mediated rearrangements of spiro[2.n]alkane-1,1-dicarboxylates (n = 2–5): an experimental evidence of stepwise 1,2-zwitter-ion formation Full article

Journal

Mendeleev Communications
ISSN: 1364-551X , E-ISSN: 0959-9436

Output data

Year: 2026, Volume: 36, Number: 4, DOI: 10.71267/mencom.7966

Authors

Borisova Irina A ¹ , Potapov Konstantin Vladislavovich ¹ , Novikov Maxim Alexandrovich ¹ , Novikov Roman Aleksandrovich ¹ , Tomilov Yury Vasil'evich ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation

The ability of TiCl4 and GaCl3 effectively mediate rearrangements of spiro[2.n]alkane-1,1-dicarboxylates (n = 2–5) to (alkylidene)malonates was shown, the mechanism involving formation of 1,2-zwitter-ion species. In the case of TiCl4, stepwise (alkylidene)malonate formation pathway was postulated that involves preliminary chloride-mediated cyclopropane ring-opening followed by 1,2-H and 1,2-alkyl migrations.

Borisova I.A. , Potapov K.V. , Novikov M.A. , Novikov R.A. , Tomilov Y.V.
Lewis acid mediated rearrangements of spiro[2.n]alkane-1,1-dicarboxylates (n = 2–5): an experimental evidence of stepwise 1,2-zwitter-ion formation
Mendeleev Communications. 2026. V.36. N4. DOI: 10.71267/mencom.7966 OpenAlex

Submitted:	Nov 7, 2025
Accepted:	Jan 22, 2026

≡ OpenAlex:

W7135211465