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Based on the carbonyl stretching frequencies of <jats:italic>cis<\/jats:italic>\u2010[RhCl(CO)<jats:sub>2<\/jats:sub>(L)] complexes, the order of electron donor ability was predicted to be CAAC<jats:sub>a<\/jats:sub>\u2248BAC<jats:sub>a<\/jats:sub>&gt;NHCs. When the betaines \u03bd<jats:sub>asym<\/jats:sub>(CO<jats:sub>2<\/jats:sub>) values are used, the apparent ordering is BAC<jats:sub>a<\/jats:sub>&gt;NHCs\u2248CAAC<jats:sub>a<\/jats:sub> that indicates a limitation for the use of IR spectroscopy in the ranking of ligand \u03c3\u2010donating ability. Although all carbenes react with carbon disulfide to give the corresponding betaines, a second equivalent of CS<jats:sub>2<\/jats:sub> reacts with the BAC\u2010CS<jats:sub>2<\/jats:sub> leading to a bicyclic thieno[2,3\u2010diamino]\u20101,3\u2010dithiole\u20102\u2010thione, which results from a novel ring expansion process. Surprisingly, in contrast to NHCs, CAAC<jats:sub><jats:bold>a<\/jats:bold><\/jats:sub> does not react with carbodiimide, whereas BAC<jats:sub>a<\/jats:sub> exclusively gives a ring expanded product, analogous to that obtained with CS<jats:sub>2<\/jats:sub>. The intermediate amidinate can be trapped, using the lithium tetrafluoroborate adduct of BAC<jats:sub>b<\/jats:sub> as a carbene surrogate.<\/jats:p>","DOI":"10.1002\/asia.200900338","type":"journal-article","created":{"date-parts":[[2009,9,24]],"date-time":"2009-09-24T14:37:09Z","timestamp":1253803029000},"page":"1745-1750","source":"Crossref","is-referenced-by-count":52,"title":["Reactivity of Cyclic (Alkyl)(amino)carbenes (CAACs) and Bis(amino)cyclopropenylidenes (BACs) with Heteroallenes: Comparisons with their <i>N<\/i>\u2010Heterocyclic Carbene (NHCs) 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