Cyclopropyl Building Blocks for Organic Synthesis, 36.  Unprecedented Addition of Dialkoxycarbenes to Tetrasubstituted Alkenes: Bicyclopropylidene and 2‐Chlorocyclopropylideneacetate | Zendy

de Meijere Armin | Zendy; Kozhushkov Sergei I. | Zendy; Yufit Dmitry S. | Zendy; Boese Roland | Zendy; Haumann Thomas | Zendy; Pole David L. | Zendy; Sharma Pradeep K. | Zendy; Warkentin John | Zendy

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Cyclopropyl Building Blocks for Organic Synthesis, 36. Unprecedented Addition of Dialkoxycarbenes to Tetrasubstituted Alkenes: Bicyclopropylidene and 2‐Chlorocyclopropylideneacetate

Author(s) -

de Meijere Armin,

Kozhushkov Sergei I.,

Yufit Dmitry S.,

Boese Roland,

Haumann Thomas,

Pole David L.,

Sharma Pradeep K.,

Warkentin John

Publication year - 1996

Publication title -

liebigs annalen

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0947-3440

DOI - 10.1002/jlac.199619960421

Subject(s) - chemistry , cyclopropane , intramolecular force , cycloaddition , heptane , nucleophile , nucleophilic addition , double bond , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , catalysis

The cycloaddition reactions of several dialkoxycarbenes generated in situ from the corresponding 2,2‐dialkoxy‐Δ 3 ‐1,3,4‐oxadiazolines of the type 3 with bicyclopropylidene 1 afford the dialkyl acetals of dispiro[2.0.2.1]heptane‐7‐one ( 4 ), whereas the analogous addition to methyl (1‐chloromethylene‐1‐carboxylate)cyclopropane 26 leads to the formation of a complex mixture of products. Those products can best be rationalized in terms of nucleophilic attack of the dialkoxycarbene on the strained CC double bond, to form a dipolar intermediate capable of a variety of intramolecular rearrangements. Several chemical transformations of the compounds of type 4 are reported.

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